Hexane → (Z)-tert-butyl (1-(5-bromo-2-fluorophenyl)-2,2-difluoroethylidene)carbamate

HRID 221755Notes

Reaction equation

[Br:1][C:2]1[CH:3]=[CH:4][C:5]([F:13])=[C:6]([C:8](=O)[CH:9]([F:11])[F:10])[CH:7]=1.[CH3:14][C:15]([O:18][C:19](=[O:40])[N:20]=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)([CH3:17])[CH3:16].CCCCCC.C1(P(=O)(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1(C)C=CC=CC=1>[C:15]([O:18][C:19](=[O:40])/[N:20]=[C:8](/[C:6]1[CH:7]=[C:2]([Br:1])[CH:3]=[CH:4][C:5]=1[F:13])\[CH:9]([F:11])[F:10])([CH3:17])([CH3:16])[CH3:14]

Participants

Conditions

Temperature: 100 °C

Procedure

A suspension of 1-(5-bromo-2-fluoro-phenyl)-2,2-difluoro-ethanone (16.0 g, 63.2 mmol) and N-(triphenylphosphoranylidene)-carbamic acid 1,1-dimethylethyl ester (CAS 68014-21-1) (26.3 g, 69.6 mmol) in 12 ml toluene was stirred at 100° C. for 2 days. The suspension became clear. After being cooled down somewhat, hexane was added till crystallization of triphenylphosphine oxide started. The mixture was filtered and the filtrate was purified by chromatography on silica gel with hexane/TBME 1-5% to give 11.37 g of the title compound as a yellow liquid.

Workup

temperatureAfter being cooled down somewhat
filtrationThe mixture was filtered
customthe filtrate was purified by chromatography on silica gel with hexane/TBME 1-5%

Sources & evidence

ORD record: ord-f0ec5f763d5d4593bfa13dcb86663496
Source dataset: uspto-grants-2012_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08207164B2

Reaction notes

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