Ethyl trifluoroacetate → N-(3-(3-bromophenyl)-3-hydroxypropyl)-2,2,2-trifluoroacetamide

HRID 341584Notes

Reaction equation

HRID 341584 reaction equation
[NH2:1][CH2:2][CH2:3][CH:4]([C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([Br:12])[CH:7]=1)[OH:5].[F:13][C:14]([F:21])([F:20])[C:15](OCC)=[O:16]>CC(OC)(C)C>[Br:12][C:8]1[CH:7]=[C:6]([CH:4]([OH:5])[CH2:3][CH2:2][NH:1][C:15](=[O:16])[C:14]([F:21])([F:20])[F:13])[CH:11]=[CH:10][CH:9]=1

Participants

4

Reactant 2

HCID 9794Ethyl trifluoroacetateHCID 576083343-Amino-1-(3-bromophenyl)propan-1-ol

Product 1

HCID 57608426N-(3-(3-bromophenyl)-3-hydroxypropyl)-2,2,2-trifluoroacetamide

Reagents, catalysts & solvents 1

HCID 15413tert-Butyl methyl etherSolvent

Procedure

To a cooled (0° C.) solution of 3-amino-1-(3-bromophenyl)propan-1-ol (24) (40 g, 173.8 mmol) in MTBE (250 mL) was added ethyl trifluoroacetate (28 mL, 234.7 mmol) over 7 min and the reaction mixture was stirred at room temperature for 50 min Concentration under reduced pressure gave trifluoroacetamide 25 as a colorless oil. Yield (55.35 g, 98%): 1H NMR (400 MHz, DMSO-d6) δ 9.33 (s, 1H), 7.51 (t, J=2.0 Hz, 1H), 7.41 (dt, J=7.6, 2.0 Hz, 1H), 7.25-7.32 (m, 2H), 5.46 (d, J=6.4 Hz, 1H), 4.55-4.60 (m, 1H), 3.20-3.23 (m, 2H), 1.75-1.82 (m, 2H).

Workup

  1. concentrationConcentration under reduced pressure

Sources & evidence

ORD record
ord-fe10228e4850493d895b6194b6fed3f9
Source dataset
uspto-grants-2014_11
Patent number
US08895782B2

Reaction notes

Loading…