Acetic Acid → 1-(2-Bromo-4-fluorophenyl)-N,N-dimethylmethanamine

HRID 558141ノート

反応式

HRID 558141 の反応式
[Br:1][C:2]1[CH:9]=[C:8]([F:10])[CH:7]=[CH:6][C:3]=1[CH:4]=O.[CH3:11][NH:12][CH3:13].C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(Cl)Cl>[Br:1][C:2]1[CH:9]=[C:8]([F:10])[CH:7]=[CH:6][C:3]=1[CH2:4][N:12]([CH3:13])[CH3:11]

参加物

6

反応物 4

HCID 176Acetic AcidHCID 674DimethylamineHCID 27733192-Bromo-4-fluorobenzaldehydeHCID 5049666Sodium triacetoxyborohydride

生成物 1

HCID 607115251-(2-Bromo-4-fluorophenyl)-N,N-dimethylmethanamine収率 79.8%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

Combine 2-bromo-4-fluorobenzaldehyde (5 g, 24.63 mmol), dimethylamine (2 M, 49.26 mL, 98.52 mmol) and acetic acid (8.47 mL, 147.78 mmol) in DCM (50 mL), and stir for 30 min. To this mixture, add sodium triacetoxyborohydride (49.26 mmol, 10.44 g) and stir overnight at RT. Wash with saturated NaHCO3 solution (100 mL), dry with aqueous saturated sodium chloride, and then dry over sodium sulfate. Filter the organics and remove the solvent under reduced pressure to give the title compound as a brownish oil (4.56 g). GCMS m/z 232 [M]+.

後処理

  1. washWash with saturated NaHCO3 solution (100 mL)
  2. dry with materialdry with aqueous saturated sodium chloride
  3. dry with materialdry over sodium sulfate
  4. filtrationFilter the organics and
  5. customremove the solvent under reduced pressure

出典と根拠

ORDレコード
ord-245b2e46db364502b518c65bc3e6d9c8
出典データセット
uspto-grants-2011_11
特許番号
US08063035B2

反応ノート

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