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2 protocols using chloromethyl methyl ether

1

Synthesis and Characterization of Iodoalkanes

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1-Iodobutane, 1-iodooctane, 1-iodododecane, 1-iodohexadecane, and 1-iodooctadecane were purchased from Tokyo Chemical Industry Corporation (Tokyo, Japan). L-Ascorbic acid (AA), L-Ascorbic acid sodium salt (AANa), acetyl chloride, chloromethyl methyl ether, potassium carbonate, hydrochloric acid (HCl), oxatomide, and p-nitrophenyl-2-acetamido-2-deoxy-β-D-glucopyranoside (PNAG) were purchased from FUJIFILM Wako Pure Chemical Corporation (Osaka, Japan). Diaion HP20 (Mitsubishi Chemical Corporation, Tokyo, Japan), Wakogel C-200 (FUJIFILM Wako Pure Chemical Corporation), Silica Gel 60 (Merck KGaA, Darmstadt, Germany), and TOYOPEARL HW-40C (Tosoh Corporation, Tokyo, Japan) were utilized for column chromatography. Monoclonal anti-dinitrophenyl antibody (DNP-IgE) and dinitrophenyl-labeled human serum albumin (DNP-HSA) were obtained from Sigma-Aldrich Co., St. Louis, MO, USA. All of the chemicals used were of the highest grade commercially available.
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2

Synthesis of Brominated Benzene Derivatives

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Starting materials for the preparation of 1 were obtained
from the following commercial source; 4-bromophenol,
3-bromopropan-1-ol, 6-bromohexan-1-ol, chloromethyl methyl ether,
triethylamine, and pentafluoroiodobenzene were purchased from FUJIFILM
Wako Pure Chemical Corporation. Trimethylsilylacetylene was obtained
from Apollo Scientific Ltd. A palladium catalyst, that is, Cl2Pd(PPh3)2, was purchased from Aldrich
Fine Chemicals. PPh3 and CuI were also purchased from FUJIFILM
Wako Pure Chemical Corporation. Column chromatography was carried
out on silica gel (Wakogel 60N, 38–100 μm), and thin-layer chromatographic (TLC) analysis was performed on
silica gel TLC plates (Merck, Silica gel 60F254). All reactions
were carried out using dried glassware and magnetic stirrer bars.
Typical synthetic procedures for V-3a and Y-4a and spectral data for the V-3 and Y-4 are
described below. In the Supporting Information are summarized all synthetic procedures and spectral data for other
compounds.
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