Benzene → HCID 25017079, compound

HRID 511973Notes

Reaction equation

HRID 511973 reaction equation
[Na+].[CH2:2]([O:9][C:10]1[CH:15]=[CH:14][C:13]([CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][S:21]([O-:24])(=O)=[O:22])=[CH:12][CH:11]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[S:25]([Cl:28])([Cl:27])=[O:26].CN(C=[O:33])C.[CH:34]1[CH:39]=CC=CC=1>>[CH2:2]([O:9][C:10]1[CH:15]=[CH:14][C:13]([CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][S:21]([Cl:27])(=[O:24])=[O:22])=[CH:12][CH:11]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[CH2:2]([O:9][C:10]1[CH:11]=[CH:12][C:13]([CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:39][CH2:34][S:25]([Cl:28])(=[O:26])=[O:33])=[CH:14][CH:15]=1)[C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1

Participants

6

Reactant 4

HCID 241BenzeneHCID 6228DimethylformamideHCID 24386Thionyl ChlorideHCID 71512046HCID 71512046, compound

Product 2

HCID 25017079HCID 25017079, compoundYield 37%HCID 25017343HCID 25017343, compound

Procedure

5-(4-Benzyloxy-phenyl)-pentanesulfonyl chloride (12.4) was synthesized as described in 12.1 using 11.4 (0.96 g, 2.85 mmol) and thionyl chloride (1.00 g, 8.55 mmol) in benzene (27 mL)/DMF (3 mL). Purification by flash column chromatography on silica gel gave the title compound (0.36 g, 37% yield from 10.4) as a white solid (m p 58-60° C.).

Workup

  1. customPurification by flash column chromatography on silica gel

Sources & evidence

ORD record
ord-4965d5c745594013b80475e7220e7047
Source dataset
uspto-grants-2015_08
Patent number
US09102622B2

Reaction notes

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