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

HRID 1777408

反応式

HRID 1777408 の反応式
[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

参加物

5

反応物 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 5081913Imd-0354

生成物 1

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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒2 回

実験手順

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%).

後処理

  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)

出典と根拠

ORDレコード
ord-40de91f884a44fcda94fb99ecc2b1564
出典データセット
uspto-grants-2016_02
特許番号
US09266872B2

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