Hydrochloric Acid → 2-Amino-2-(3-bromo-phenyl)-3,3-difluoro-propan-1-ol hydrochloride

HRID 221687Notes

Reaction equation

HRID 221687 reaction equation
C(OC(=O)[NH:7][C:8]([C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([Br:20])[CH:15]=1)([CH2:12][OH:13])[CH:9]([F:11])[F:10])(C)(C)C.[ClH:22]>O1CCOCC1>[ClH:22].[NH2:7][C:8]([C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([Br:20])[CH:15]=1)([CH:9]([F:10])[F:11])[CH2:12][OH:13]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 66665609[1-(3-Bromo-phenyl)-2,2-difluoro-1-hydroxymethyl-ethyl]-carbamic acid tert-butyl ester

Product 1

HCID 666658812-Amino-2-(3-bromo-phenyl)-3,3-difluoro-propan-1-ol hydrochloride

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

[1-(3-Bromo-phenyl)-2,2-difluoro-1-hydroxymethyl-ethyl]-carbamic acid tert-butyl ester (8.408 g, 22.96 mmol) was dissolved in 105 ml 4 N HCl in dioxane. The reaction was stirred for 45 min. After completion volatiles were removed under reduced pressure to yield a white solid. 1H-NMR (360 MHz, DMSO-d6): 9.30 (br, 3H, NH3+), 7.85 (s, 1H), 7.70 (d, 1H), 7.60 (d, 1H), 7.49 (t, 1H), 6.63 (t, 1H, CHF2), 6.03 (br, 1H), 4.05 (m, 2H); MS: 266 [(M+H)+].

Workup

  1. customAfter completion volatiles were removed under reduced pressure
  2. customto yield a white solid

Sources & evidence

ORD record
ord-cfbcee8f06ef460fa6877999c40a31ca
Source dataset
uspto-grants-2012_06
Patent number
US08207164B2

Reaction notes

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