Methylamine → (2-Bromo-3-fluoro-6-nitrophenyl)methylamine

HRID 243185Notes

Reaction equation

HRID 243185 reaction equation
CN.[Br:3][C:4]1[C:9](F)=[C:8]([N+:11]([O-:13])=[O:12])[CH:7]=[CH:6][C:5]=1[F:14].C[CH2:16][N:17](C(C)C)C(C)C>C1COCC1>[Br:3][C:4]1[C:5]([F:14])=[CH:6][CH:7]=[C:8]([N+:11]([O-:13])=[O:12])[C:9]=1[CH2:16][NH2:17]

Participants

5

Reactant 3

HCID 6329MethylamineHCID 81531DiisopropylethylamineHCID 137327452-Bromo-1,3-difluoro-4-nitrobenzene

Product 1

HCID 68157229(2-Bromo-3-fluoro-6-nitrophenyl)methylamineYield 91.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Methylamine (2M in THF, 19 mL, 38.1 mmol) was added to a solution of 2-bromo-1,3-difluoro-4-nitrobenzene (4.53 g, 19 mmol) and DIPEA (6.8 mL, 38.1 mmol) in THF (70 mL) and the resultant mixture stirred at 60° C. for 3 h. The reaction mixture was concentrated in vacuo and the residue purified by chromatography eluting with (SiO2 0-80% DCM in cyclohexane) to give title compound as an orange/yellow solid (4.32 g, 91%). LCMS (Method C): RT 3.46 min [M+H]+ 249.0, 251.0.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customthe residue purified by chromatography
  3. washeluting with (SiO2 0-80% DCM in cyclohexane)

Sources & evidence

ORD record
ord-97e3b0a0e1b14419b3bb23f6c34ccc5b
Source dataset
uspto-grants-2014_02
Patent number
US08653089B2

Reaction notes

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