Sodium Hydroxide → 2-(3-Chlorophenyl)-2,2-difluoroethan-1-amine

HRID 1987056Notes

Reaction equation

HRID 1987056 reaction equation
Cl.[Cl:2][C:3]1[CH:4]=[C:5]([C:9]([F:13])([F:12])[CH2:10][NH2:11])[CH:6]=[CH:7][CH:8]=1.[OH-].[Na+]>>[Cl:2][C:3]1[CH:4]=[C:5]([C:9]([F:12])([F:13])[CH2:10][NH2:11])[CH:6]=[CH:7][CH:8]=1

Participants

3

Reactant 2

HCID 14798Sodium HydroxideHCID 688270912-(3-Chlorophenyl)-2,2-difluoroethylamine hydrochloride

Product 1

HCID 577226982-(3-Chlorophenyl)-2,2-difluoroethan-1-amineYield 103.9%

Procedure

2-(3-chlorophenyl)-2,2-difluoroethylamine hydrochloride (1.65 g, 7.23 mmol), as prepared in the previous step, was taken up with 2.5 M NaOH (4 mL) and extracted with ether (1×8 mL, 1×4 mL). The combined organic layers were dried (Na2SO4) and briefly concentrated to provide 1.44 g (quant. yield) of the title compound as a clear dark brown oil. 1H NMR (300 MHz, CDCl3) δ 7.48 (br, 1H), 7.46-7.41 (m, 1H), 7.40-7.34 (m, 2H), 3.17 (t, J=14.5 Hz, 2H), 1.29 (br, 2H).

Workup

  1. extractionextracted with ether (1×8 mL, 1×4 mL)
  2. dry with materialThe combined organic layers were dried (Na2SO4)
  3. concentrationbriefly concentrated

Sources & evidence

ORD record
ord-f8fa0fa76eb14b0db21e372013c52708
Source dataset
uspto-grants-2009_06
Patent number
US07550474B2

Reaction notes

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