Ethyl 2-(2,2-Difluoroethyl)oxy-5-nitro-benzoate → Ethyl 5-amino-2-(2,2-difluoroethyl)oxy-benzoate

HRID 1846085Notes

Reaction equation

HRID 1846085 reaction equation
[F:1][CH:2]([F:19])[CH2:3][O:4][C:5]1[CH:15]=[CH:14][C:13]([N+:16]([O-])=O)=[CH:12][C:6]=1[C:7]([O:9][CH2:10][CH3:11])=[O:8]>CO.[Pd]>[NH2:16][C:13]1[CH:14]=[CH:15][C:5]([O:4][CH2:3][CH:2]([F:1])[F:19])=[C:6]([CH:12]=1)[C:7]([O:9][CH2:10][CH3:11])=[O:8]

Participants

4

Reactant 1

HCID 86658666Ethyl 2-(2,2-Difluoroethyl)oxy-5-nitro-benzoate

Product 1

HCID 58483394Ethyl 5-amino-2-(2,2-difluoroethyl)oxy-benzoate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of ethyl 2-(2,2-difluoroethyl)oxy-5-nitro-benzoate (600 mg, 2.18 mmol) and 80 mg 10% Pd/C in 30 mL MeOH was stirred for 6.5 h under an atmosphere of hydrogen (3 bar). After filtration and concentration i. vac. the subtitle compound was obtained. Yield: 500 mg, (94%). MS [M+H]+=246; TLC: Rf=0.2 (silica gel, DCM:EtOH 99:1).

Workup

  1. filtrationAfter filtration and concentration i

Sources & evidence

ORD record
ord-d9171c87bed744ee98b6543814e83ab3
Source dataset
uspto-grants-2015_02
Patent number
US08951999B2

Reaction notes

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