Benzyl Bromide → 2-benzyloxy-N-[3,5-bis(trifluoromethyl)phenyl]-5-chloro-benzamide

HRID 1777408

반응식

HRID 1777408 반응식
[F:1][C:2]([F:25])([F:24])[C:3]1[CH:4]=[C:5]([NH:13][C:14](=[O:23])[C:15]2[CH:20]=[C:19]([Cl:21])[CH:18]=[CH:17][C:16]=2[OH:22])[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1.[CH2:26](Br)[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[CH2:26]([O:22][C:16]1[CH:17]=[CH:18][C:19]([Cl:21])=[CH:20][C:15]=1[C:14]([NH:13][C:5]1[CH:6]=[C:7]([C:9]([F:10])([F:11])[F:12])[CH:8]=[C:3]([C:2]([F:1])([F:24])[F:25])[CH:4]=1)=[O:23])[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

참가 물질

5

반응물 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 5081913Imd-0354

생성물 1

HCID 715085922-benzyloxy-N-[3,5-bis(trifluoromethyl)phenyl]-5-chloro-benzamide수율 93%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매2회

실험 절차

N-(3,5-bis(trifluoromethyl)phenyl)-5-chloro-2-hydroxybenzamide (191.8 mg) obtained in step 1 was dissolved in dimethylformamide (DMF, 1.5 ml), to which benzylbromide (0.07 ., 0.55 mmol) and potassium carbonate (K2CO3, 82.9 mg, 0.6 mmol) were added. The reaction mixture was stirred at room temperature for 4 hours. Dimethylformamide was distillated under reduced pressure, followed by extraction with ethylacetate (EtOAc). The extracted organic layer was dried over MgSO4, filtered and concentrated. The concentrated reactant was separated by column chromatography (developing solvent: hexane/ethylacetate=15/1) to give 220 mg of the target compound (yield: 93%).

후처리

  1. additionwere added
  2. extractionfollowed by extraction with ethylacetate (EtOAc)
  3. dry with materialThe extracted organic layer was dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe concentrated reactant was separated by column chromatography (developing solvent: hexane/ethylacetate=15/1)

출처 및 근거

ORD 기록
ord-40de91f884a44fcda94fb99ecc2b1564
출처 데이터셋
uspto-grants-2016_02
특허 번호
US09266872B2

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