1-(Benzyloxy)-2,3-difluoro-4-nitrobenzene → 4-Amino-2,3-difluorophenol

HRID 872961Notes

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

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-6f31330ceedd4d8c8cb84fc2b97066ad
Source dataset: uspto-grants-2015_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08975282B2

Reaction notes

Loading…