Hydrochloric Acid → HCID 18424393, 화합물

HRID 1282414

반응식

HRID 1282414 반응식
Br[C:2]1[CH:3]=[C:4]([C:9]([F:12])([F:11])[F:10])[CH:5]=[CH:6][C:7]=1[Cl:8].[F:13][CH2:14][C:15]([CH2:19][F:20])([OH:18])[CH:16]=[CH2:17].C(=O)([O-])[O-].[K+].[K+].Cl>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.CN(C)C(=O)C>[Cl:8][C:7]1[CH:6]=[CH:5][C:4]([C:9]([F:12])([F:11])[F:10])=[CH:3][C:2]=1/[CH:17]=[CH:16]/[C:15]([CH2:19][F:20])([OH:18])[CH2:14][F:13]

참가 물질

8

반응물 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 679882-Bromo-1-chloro-4-(trifluoromethyl)benzeneHCID 18424424HCID 18424424, 화합물

생성물 1

HCID 18424393HCID 18424393, 화합물수율 88%

시약·촉매·용매 3

HCID 74236Tetrabutylammonium Bromide촉매HCID 167845palladium(II) acetate촉매HCID 31374Dimethylacetamide용매

반응 조건

온도
80 °C

실험 절차

A mixture of 3-bromo-4-chlorobenzotrifluoride (1.50 g), 1-fluoro-2-fluoromethyl-3-buten-2-ol (0.80 g), potassium carbonate (2.10 g), tetrabutylammonium bromide (325 mg), palladium acetate (56 mg) and N,N-dimethylacetamide (10 ml) was stirred under a nitrogen atmosphere at 80° C. for 14 hours. To the reaction mixture, 1 N HCl was added followed by extraction with a hexane/ethyl acetate mixed (1/1) solvent; the resulting organic layers were combined and washed with a saturated aqueous solution of sodium thiosulfate and a saturated aqueous solution of sodium chloride; the mixture was dried with anhydrous sodium sulfate and concentrated under reduced pressure; the resulting residue was subjected to silica gel column chromatography (eluent; hexane/ethyl acetate=10/1) to give 4-(2-chloro-5-trifluoromethylphenyl)-1-fluoro-2-fluoromethyl-3-trans-buten-2-ol (1.53 g) having a melting point of 61-62° C.

후처리

  1. extractionfollowed by extraction with a hexane/ethyl acetate
  2. additionmixed (1/1) solvent
  3. washwashed with a saturated aqueous solution of sodium thiosulfate
  4. dry with materialthe mixture was dried with anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-745a1a71b5384500b36d56cf9bbe7072
출처 데이터셋
uspto-grants-2002_09
특허 번호
US06455708B1

연결된 노트

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