Benzenamine, 3,5-bis(trifluoromethyl)- → 2-[3,5-Bis(trifluoromethyl)anilino]ethan-1-ol

HRID 2047463Notes

Reaction equation

HRID 2047463 reaction equation
[F:1][C:2]([F:15])([F:14])[C:3]1[CH:4]=[C:5]([CH:7]=[C:8]([C:10]([F:13])([F:12])[F:11])[CH:9]=1)[NH2:6].Br[CH2:17][CH2:18][OH:19]>>[F:1][C:2]([F:14])([F:15])[C:3]1[CH:4]=[C:5]([NH:6][CH2:17][CH2:18][OH:19])[CH:7]=[C:8]([C:10]([F:11])([F:12])[F:13])[CH:9]=1

Participants

3

Reactant 2

HCID 9480Benzenamine, 3,5-bis(trifluoromethyl)-HCID 108982-Bromoethanol

Product 1

HCID 201299412-[3,5-Bis(trifluoromethyl)anilino]ethan-1-olYield 58%

Procedure

A solution of 3,5-bis(trifluoromethyl)aniline (4.6 g) in 2-bromoethanol (25.0 g) was stirred at 70° C. for 14 hr, and concentrated under reduced pressure. The residue was poured into water, and the mixture was extracted with ethyl acetate. The extract was washed with saturated aqueous sodium hydrogen carbonate solution, water and saturated brine, dried and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (33% ethyl acetate/hexane) to give 2-{[3,5-bis(trifluoromethyl)phenyl]amino}ethanol (3.1 g, 58%) as a brown powder.

Workup

  1. concentrationconcentrated under reduced pressure
  2. additionThe residue was poured into water
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe extract was washed with saturated aqueous sodium hydrogen carbonate solution, water and saturated brine
  5. customdried
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (33% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-7a0e0d272a0d431380d919550ac5281e
Source dataset
uspto-grants-2013_11
Patent number
US08592454B2

Reaction notes

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