1-(Benzyloxy)-2,3-difluoro-4-nitrobenzene → 4-Amino-2,3-difluorophenol
Reaction equation
C([O:8][C:9]1[CH:14]=[CH:13][C:12]([N+:15]([O-])=O)=[C:11]([F:18])[C:10]=1[F:19])C1C=CC=CC=1>CO.C1COCC1.[Pd]>[NH2:15][C:12]1[CH:13]=[CH:14][C:9]([OH:8])=[C:10]([F:19])[C:11]=1[F:18]Participants
5
Reactant 1
Product 1
Reagents, catalysts & solvents 3
Conditions
- Temperature
- 32 °C
Procedure
To a suspension of 1-(benzyloxy)-2,3-difluoro-4-nitrobenzene (1.93 g, 0.73 mmol) in CH3OH (45 mL) and THF (9 mL) was added Pd/C (333 mg, 6% Pd content, 53%˜55% water content). The mixture was stirred at 32° C. for 13 hours under H2 atmosphere. The mixture was filtered through a CELITE® pad, which was washed with 50 mL of EtOAc. The filtrate was concentrated in vacuo, washed with 30 mL of CH2Cl2 to give the title compound as a dark brown solid (0.89 g, 84%).
Workup
- filtrationThe mixture was filtered through a CELITE® pad, which
- washwas washed with 50 mL of EtOAc
- concentrationThe filtrate was concentrated in vacuo
- washwashed with 30 mL of CH2Cl2
Sources & evidence
- ORD record
- ord-f6d1278c460d4baca81bf9e802fa77d5
- Source dataset
- uspto-grants-2016_05
- Patent number
- US09326975B2
Reaction notes
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