Borane → 2,2-Difluoro-2-phenylethylamine

HRID 216201Notes

Reaction equation

HRID 216201 reaction equation
[F:1][C:2]([F:12])([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)[C:3]([NH2:5])=O.B>C1COCC1>[F:1][C:2]([F:12])([C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=1)[CH2:3][NH2:5]

Participants

4

Reactant 2

HCID 6331BoraneHCID 2696562,2-Difluoro-2-phenylacetamide

Product 1

HCID 126355292,2-Difluoro-2-phenylethylamineYield 83.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a s solution of 2,2-difluoro-2-phenyl-acetamide (0.76 g, 4.4 mmol) in THF (5 mL) is added Borane in THF (1 M, 20 mL, 20 mmole) at 10° C. After 70° C. for 20 h, the mixture is quenched with water (10 mL), concentrated, and chromatographed on SiO2 eluting with 90% EtOAc in heptane to afford 2,2-difluoro-2-phenyl-ethylamine (0.58 g). LCMS: RT 0.92 minutes; MS: 158 (M+H); 1H NMR (300 MHz, CDCl3) □7.57-7.45 (5H, m), 3.2 (2H, t).

Workup

  1. customthe mixture is quenched with water (10 mL)
  2. concentrationconcentrated
  3. customchromatographed on SiO2 eluting with 90% EtOAc in heptane

Sources & evidence

ORD record
ord-b97788bfe55049ee95ec4cff09ce1d8d
Source dataset
uspto-grants-2012_06
Patent number
US08193183B2

Reaction notes

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