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

HRID 558141Notes

Reaction equation

HRID 558141 reaction equation
[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]

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

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]+.

Workup

  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

Sources & evidence

ORD record
ord-245b2e46db364502b518c65bc3e6d9c8
Source dataset
uspto-grants-2011_11
Patent number
US08063035B2

Reaction notes

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