3-Phenoxyaniline → 3-[(n-3-Phenoxy-phenyl)amino]1,1,1-trifluoro-2-propanol

HRID 1884632Notes

Reaction equation

HRID 1884632 reaction equation
[O:1]([C:8]1[CH:9]=[C:10]([CH:12]=[CH:13][CH:14]=1)[NH2:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[F:15][C:16]([F:21])([F:20])[CH:17]1[O:19][CH2:18]1>>[O:1]([C:8]1[CH:9]=[C:10]([NH:11][CH2:18][CH:17]([OH:19])[C:16]([F:21])([F:20])[F:15])[CH:12]=[CH:13][CH:14]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 771353-PhenoxyanilineHCID 5207692-(Trifluoromethyl)oxirane

Product 1

HCID 235060633-[(n-3-Phenoxy-phenyl)amino]1,1,1-trifluoro-2-propanolYield 71%

Conditions

Temperature
100 °C

Procedure

EX-588B) A mixture of solid 3-phenoxyaniline (2.96 g, 16 mmol) and 1,1,1-trifluoro-2,3-epoxypropane (1.30 mL, 15.0 mmol) was placed in a sealed tube and heated to 100° C. giving a dark solution. The stirred solution was heated 18 h and cooled to give a dark oil. Purification by flash chromatography on silica gel eluting with dichloromethane gave 3.15 g (71%) of the desired 3-[(N-3-phenoxy-phenyl)amino]-1,1,1-trifluoro-2-propanol product as a colorless oil.

Workup

  1. customwas placed in a sealed tube
  2. customgiving a dark solution
  3. temperatureThe stirred solution was heated 18 h
  4. temperaturecooled
  5. customto give a dark oil
  6. customPurification by flash chromatography on silica gel eluting with dichloromethane

Sources & evidence

ORD record
ord-eb7472bae4904862b7241ba5765b5405
Source dataset
uspto-grants-2004_07
Patent number
US06765023B2

Reaction notes

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