Carbon Dioxide → 2-(tert-Butoxycarbonyl)-6-chloro-4-trifluoromethylbenzoic acid

HRID 1449577

反応式

HRID 1449577 の反応式
C(OC(N[C:9]1[CH:14]=[C:13]([C:15]([F:18])([F:17])[F:16])[CH:12]=[C:11]([Cl:19])[CH:10]=1)=O)(C)(C)C.[C:20]([Li])([CH3:23])([CH3:22])[CH3:21].[C:25](=[O:27])=[O:26].[OH2:28].[O:29]1[CH2:33]CCC1>CCCCC>[C:20]([O:26][C:25]([C:9]1[CH:14]=[C:13]([C:15]([F:16])([F:17])[F:18])[CH:12]=[C:11]([Cl:19])[C:10]=1[C:33]([OH:29])=[O:28])=[O:27])([CH3:23])([CH3:22])[CH3:21]

参加物

7

反応物 5

HCID 280Carbon DioxideHCID 962WaterHCID 8028TetrahydrofuranHCID 18929880tert-butyl N-[3-chloro-5-(trifluoromethyl)phenyl]carbamateHCID 178418306HCID 178418306、化合物

生成物 1

HCID 189299472-(tert-Butoxycarbonyl)-6-chloro-4-trifluoromethylbenzoic acid収率 82%

試薬・触媒・溶媒 1

HCID 8003Pentane溶媒

反応条件

温度
-75 °C

実験手順

To a cold (-100° C.) stirred solution of N-(tert-butoxycarbonyl)-3-chloro-5-trifluoromethylaniline 93.4 g, 11.5 mM) in dry tetrahydrofuran (30 mL) under a nitrogen atmosphere was added dropwise t-butyllithium (14.2 mL of 1.7M solution, 24.2 mM) in pentane. The temperature of the reaction mixture was maintained at -103° to -98° C. during the addition and for 3.25 hr after the addition was completed. Crushed Dry Ice was then added to the cold reaction mixture which, after being allowed to warm to -75° C., was poured into water. The resulting mixture was extracted with ethyl acetate and the combined extracts were dried (MgSO4), filtered and concentrated to leave (3.2 g, 82%) the title compound as a solid white foam.

後処理

  1. temperatureThe temperature of the reaction mixture was maintained at -103° to -98° C. during the addition and for 3.25 hr
  2. additionafter the addition
  3. extractionThe resulting mixture was extracted with ethyl acetate
  4. dry with materialthe combined extracts were dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated

出典と根拠

ORDレコード
ord-fbe886a1c4e449dc8d59f3693e9f7c69
出典データセット
uspto-grants-1997_02
特許番号
US05599814

関連ノート

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