Trifluoroacetic acid → 1-Benzyl-3-bromobenzene

HRID 229370

反応式

HRID 229370 の反応式
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

参加物

6

反応物 4

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

生成物 1

HCID 5975321-Benzyl-3-bromobenzene収率 92.8%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-d2442339c33a4387b78e5c439d9e60e7
出典データセット
uspto-grants-2009_07
特許番号
US07563796B2

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