Water → Methyl 3,5-difluoro-2-nitrobenzoate

HRID 1845056Notes

Reaction equation

HRID 1845056 reaction equation
[F:1][C:2]1[C:3]([N+:12]([O-:14])=[O:13])=[C:4]([CH:8]=[C:9]([F:11])[CH:10]=1)[C:5]([OH:7])=[O:6].CI.[C:17]([O-])([O-])=O.[Na+].[Na+].O>CN(C=O)C.CCOC(C)=O>[CH3:17][O:6][C:5](=[O:7])[C:4]1[CH:8]=[C:9]([F:11])[CH:10]=[C:2]([F:1])[C:3]=1[N+:12]([O-:14])=[O:13]

Participants

7

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 10340Sodium CarbonateHCID 27833653,5-difluoro-2-nitrobenzoic acid

Product 1

HCID 46311132Methyl 3,5-difluoro-2-nitrobenzoate

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

6.0 g (30.0 mmol) of 3,5-difluoro-2-nitro-benzoic acid was dissolved in DMF, treated with 8.5 g (60.0 mmol) of MeI and 9.5 g (90.0 mmol) of Na2CO3, and heated at 80° C. for 2 h. Water was added to the reaction mixture, and extraction with EtOAc produced 3,5-difluoro-2-nitro-benzoic acid methyl ester. LCMS: 218 (M+1)+.

Sources & evidence

ORD record
ord-e3656fba00e64fa1828a52b9e7d889cc
Source dataset
uspto-grants-2015_02
Patent number
US08946259B2

Reaction notes

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