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

HRID 221755

반응식

HRID 221755 반응식
[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]

참가 물질

6

반응물 4

HCID 8058HexaneHCID 13097Triphenylphosphine OxideHCID 2756802N-Boc-Imino-(triphenyl)phosphoraneHCID 548578331-(5-Bromo-2-fluorophenyl)-2,2-difluoroethanone

생성물 1

HCID 87096325(Z)-tert-butyl (1-(5-bromo-2-fluorophenyl)-2,2-difluoroethylidene)carbamate수율 51.1%

시약·촉매·용매 1

HCID 1140Toluene용매

반응 조건

온도
100 °C

실험 절차

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.

후처리

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

출처 및 근거

ORD 기록
ord-f0ec5f763d5d4593bfa13dcb86663496
출처 데이터셋
uspto-grants-2012_06
특허 번호
US08207164B2

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