Water → 2-Benzyloxy-5-(2-bromoacetyl)-N-[3,5-bis(trifluoromethyl)phenyl]benzamide

HRID 644411노트

반응식

HRID 644411 반응식
[C:1]([C:4]1[CH:5]=[CH:6][C:7]([O:27][CH2:28][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)=[C:8]([CH:26]=1)[C:9]([NH:11][C:12]1[CH:17]=[C:16]([C:18]([F:21])([F:20])[F:19])[CH:15]=[C:14]([C:22]([F:25])([F:24])[F:23])[CH:13]=1)=[O:10])(=[O:3])[CH3:2].[Br-:35].[Br-].[Br-].C1([N+](C)(C)C)C=CC=CC=1.C1([N+](C)(C)C)C=CC=CC=1.C1([N+](C)(C)C)C=CC=CC=1.O>O1CCCC1>[CH2:28]([O:27][C:7]1[CH:6]=[CH:5][C:4]([C:1](=[O:3])[CH2:2][Br:35])=[CH:26][C:8]=1[C:9]([NH:11][C:12]1[CH:17]=[C:16]([C:18]([F:20])([F:19])[F:21])[CH:15]=[C:14]([C:22]([F:25])([F:24])[F:23])[CH:13]=1)=[O:10])[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1

참가 물질

5

반응물 3

HCID 962WaterHCID 178602005-Acetyl-2-benzyloxy-N-[3,5-bis(trifluoromethyl)phenyl]benzamideHCID 17977687Phenyltrimethylammonium bromide dibromide

생성물 1

HCID 178603042-Benzyloxy-5-(2-bromoacetyl)-N-[3,5-bis(trifluoromethyl)phenyl]benzamide수율 42.7%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

5-Acetyl-2-benzyloxy-N-[3,5-bis(trifluoromethyl)phenyl]benzamide (compound of Example 58(3); 4.81 g, 10 mmol) was dissolved in tetrahydrofuran (30 ml). Phenyltrimethylammonium tribromide (3.75 g, 10 mmol) was added, and the mixture was stirred at room temperature for 12 hours. The reaction mixture was poured into water and extracted with ethyl acetate. After the organic layer was washed with aqueous sodium hydrogen sulfite, water and brine, dried over anhydrous magnesium sulfate, the residue obtained by evaporation under reduced pressure was purified by chromatography on silica gel (n-hexane:ethyl acetate=4:1), and recrystallized (ethyl acetate/n-hexane) to give the title compound (2.39 g, 42.7%) as a white solid.

후처리

  1. extractionextracted with ethyl acetate
  2. washAfter the organic layer was washed with aqueous sodium hydrogen sulfite, water and brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customthe residue obtained by evaporation under reduced pressure
  5. customwas purified by chromatography on silica gel (n-hexane:ethyl acetate=4:1)
  6. customrecrystallized (ethyl acetate/n-hexane)

출처 및 근거

ORD 기록
ord-f4b90b6288af44698a204e12171a05d3
출처 데이터셋
uspto-grants-2010_04
특허 번호
US07700655B2

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