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

HRID 3129

反応式

HRID 3129 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 1.7 M 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-1eb43454a5ef481dbf4ca95331913c1b
出典データセット
uspto-grants-1998_03
特許番号
US05733910

関連ノート

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