Thionyl Chloride → Methyl 5-bromo-2-(2-fluorophenylamino)-3,4-difluorobenzoate

HRID 928939Notes

Reaction equation

HRID 928939 reaction equation
[Br:1][C:2]1[C:3]([F:20])=[C:4]([F:19])[C:5]([NH:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[F:18])=[C:6]([CH:10]=1)[C:7]([OH:9])=[O:8].O=S(Cl)Cl.S1(CCC[CH2:28]1)(=O)=O>C(O)C.CO.CN1C(=O)N(C)CCC1.CN(P(N(C)C)(N(C)C)=O)C.CS(C)=O.CCOCC>[Br:1][C:2]1[C:3]([F:20])=[C:4]([F:19])[C:5]([NH:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[F:18])=[C:6]([CH:10]=1)[C:7]([O:9][CH3:28])=[O:8]

Participants

10

Reactant 3

HCID 24386Thionyl ChlorideHCID 31347SulfolaneHCID 595193885-Bromo-3,4-difluoro-2-((2-fluorophenyl)amino)benzoic acid

Product 1

HCID 59519391Methyl 5-bromo-2-(2-fluorophenylamino)-3,4-difluorobenzoate

Reagents, catalysts & solvents 6

HCID 679Dimethyl SulfoxideSolventHCID 702EthanolSolventHCID 887MethanolSolvent2×HCID 3283Diethyl EtherSolventHCID 12679HexamethylphosphoramideSolventHCID 816462(1H)-Pyrimidinone, tetrahydro-1,3-dimethyl-Solvent

Procedure

5-Bromo-3,4-difluoro-2-((2-fluorophenyl)amino)benzoic acid can be reacted with MeOH in the presence of SOCl2 in appropriate solvent (include aliphatic and aromatic hydrocarbon (such as pentane, hexane, heptane, cyclohexane, petroleum ether, petrol, gasoline, benzene, toluene, xylene), aliphatic and aromatic halo-hydrocarbon (such as dichloromethane, 1,2-dichloroethane, chloroform, phenixin, chlorobenzene, o-dichlorobenzene), ether (such as diethyl ether, dibutyl ether, glycol dimethyl ether, 2-methoxyethyl ether, tetrahydrofuran, dioxane), ketone (such as acetone, methyl ethyl ketone, methyl isopropyl ketone, methyl isobutyl ketone), ester (such as ethyl acetate, methyl acetate), nitrile (such as acetonitrile, propiononitrile), amide (such as N,N-dimethylformamide, N,N-dimethylacetamide and N-methylpyrrolidin-2-one), DMSO, sulfolane, HMPA, DMPU, prefer methanol and ethanol). The reaction proceeds for several hours (3-12 h, prefer 5-10 h). Methyl 5-bromo-3,4-difluoro-2-((2-fluorophenyl)amino)benzoate is obtained after conventional workup.

Workup

  1. waitThe reaction proceeds for several hours
  2. custom(3-12 h, prefer 5-10 h)

Sources & evidence

ORD record
ord-a9b169dbae4a4bdc9fe9d454c9eee33d
Source dataset
uspto-grants-2016_03
Patent number
US09290468B2

Reaction notes

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