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

HRID 1449577노트

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HRID 1449577 반응식
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]

참가 물질

7

반응물 5

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

생성물 1

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

시약·촉매·용매 1

HCID 8003Pentane용매

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온도
-75 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-fbe886a1c4e449dc8d59f3693e9f7c69
출처 데이터셋
uspto-grants-1997_02
특허 번호
US05599814

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