1-[2-[(6-Bromohexyl)oxy]-1,1-difluoroethyl]-3-methylbenzene → 2-{6-[2,2-Difluoro-2-(3-methylphenyl)ethoxy]hexyl}-1H-isoindole-1,3(2H)-dione

HRID 1966633Notes

Reaction equation

HRID 1966633 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][O:8][CH2:9][C:10]([C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([CH3:19])[CH:14]=1)([F:12])[F:11].FC(F)(C1C=CC=CC=1)COCCCCCC[N:30]1[C:38](=[O:39])[C:37]2[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=2)[C:31]1=[O:40]>>[F:11][C:10]([F:12])([C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([CH3:19])[CH:14]=1)[CH2:9][O:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][N:30]1[C:38](=[O:39])[C:37]2[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=2)[C:31]1=[O:40]

Participants

3

Reactant 2

HCID 672456761-[2-[(6-Bromohexyl)oxy]-1,1-difluoroethyl]-3-methylbenzeneHCID 672458672-[6-(2,2-Difluoro-2-phenylethoxy)hexyl]-1H-isoindole-1,3(2H)-dione

Product 1

HCID 672465922-{6-[2,2-Difluoro-2-(3-methylphenyl)ethoxy]hexyl}-1H-isoindole-1,3(2H)-dioneYield 40%

Procedure

Obtained from Intermediate 30 (8.77 g, 26.2 mmol) by the procedure described in Intermediate 8. Purification by column chromatography with silica gel and methylene chloride as eluent gave the title compound (4.0 g, 40%) as oil.

Workup

  1. customPurification by column chromatography with silica gel and methylene chloride as eluent

Sources & evidence

ORD record
ord-398b98d7ab504e038f72cedb9ca343ff
Source dataset
uspto-grants-2013_04
Patent number
US08420669B2

Reaction notes

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