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

HRID 2196309

反応式

HRID 2196309 の反応式
[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]

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

反応条件

温度
100 °C

実験手順

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.

後処理

  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%

出典と根拠

ORDレコード
ord-5c131a8a8afe4d80a12fc8f74aabd2da
出典データセット
uspto-grants-2012_12
特許番号
US08338413B1

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