2-Aminophenol → HCID 66835936, compound

HRID 2404483Notes

Reaction equation

HRID 2404483 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C:9]([F:12])([F:11])[F:10])=[CH:4][C:3]=1[CH:13]([OH:17])[C:14]([OH:16])=O.[NH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1O>C1(C)C(C)=CC=CC=1>[O:16]1[C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=2[N:18]=[C:14]1[CH:13]([C:3]1[CH:4]=[C:5]([O:8][C:9]([F:10])([F:11])[F:12])[CH:6]=[CH:7][C:2]=1[F:1])[OH:17]

Participants

4

Reactant 2

HCID 58012-AminophenolHCID 66836075HCID 66836075, compound

Product 1

HCID 66835936HCID 66835936, compound

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

A mixture of (2-fluoro-5-trifluoromethoxyphenyl)hydroxyacetic acid (prepared according to 72C) (2.4 g), ortho-aminophenol (1.03 g) in xylene (25 mL) is refluxed for 4 h with a Dean-Stark apparatus and concentrated under reduced pressure. Purification by chromatography on silica gel (gradient dichloromethane/methanol/ammonia from 100/0/0 to 98/2/0.5) to afford the pure benzoxazol-2-yl(2-fluoro-5-trifluoromethoxyphenyl)methanol.

Workup

  1. temperatureis refluxed for 4 h with a Dean-Stark apparatus
  2. concentrationconcentrated under reduced pressure
  3. customPurification by chromatography on silica gel (gradient dichloromethane/methanol/ammonia from 100/0/0 to 98/2/0.5)

Sources & evidence

ORD record
ord-da1eb4ea8b1443d08cc3128b67611671
Source dataset
uspto-grants-2014_08
Patent number
US08802664B2

Reaction notes

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