Trifluoroacetic acid → 1-Benzyl-3-bromobenzene

HRID 229370

반응식

HRID 229370 반응식
FC(F)(F)C(O)=O.[Br:8][C:9]1[CH:10]=[C:11]([CH:20]=[CH:21][CH:22]=1)[C:12]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=O.[BH4-].[Na+].[OH-].[Na+]>C(Cl)Cl>[CH2:12]([C:11]1[CH:20]=[CH:21][CH:22]=[C:9]([Br:8])[CH:10]=1)[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

참가 물질

6

반응물 4

HCID 6422Trifluoroacetic acidHCID 14798Sodium HydroxideHCID 705483-BromobenzophenoneHCID 4311764Sodium borohydride

생성물 1

HCID 5975321-Benzyl-3-bromobenzene수율 92.8%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

Under a nitrogen atmosphere, into a cold (10° C.) solution of trifluoroacetic acid (240 mL) was added a solution of 3-bromobenzophenone (11 g, 42.1 mmol) in CH2Cl2 (120 mL) over 10 minutes, followed by slow addition of NaBH4-pellets (19 g) over 1 hour. The reaction mixture was stirred at room temperature for 18 h, poured into ice, basified with NaOH (50%) to pH 8 and extracted with ether. The organic extracts were combined, dried over MgSO4, treated with charcoal and filtered. The filtrate was concentrated in vacuo to give 1-benzyl-3-bromobenzene as an oil (9.65 g, 92% yield) MS m/e (M+H)+ 248; 1H NMR (400 MHZ, DMSOd6) δ 3.89 (s, 2H,), 7.19-7.39 (m, 9H).

후처리

  1. additionpoured into ice
  2. extractionextracted with ether
  3. dry with materialdried over MgSO4
  4. additiontreated with charcoal
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated in vacuo

출처 및 근거

ORD 기록
ord-d2442339c33a4387b78e5c439d9e60e7
출처 데이터셋
uspto-grants-2009_07
특허 번호
US07563796B2

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