Ethanol → Ethyl 2,4-difluoro-3-methoxybenzoate

HRID 1865172Notes

Reaction equation

HRID 1865172 reaction equation
[F:1][C:2]1[C:10]([O:11][CH3:12])=[C:9]([F:13])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].CN(C)C=O.S(Cl)(Cl)=O.[CH2:23](O)[CH3:24]>C1(C)C=CC=CC=1>[F:1][C:2]1[C:10]([O:11][CH3:12])=[C:9]([F:13])[CH:8]=[CH:7][C:3]=1[C:4]([O:6][CH2:23][CH3:24])=[O:5]

Participants

6

Reactant 4

HCID 702EthanolHCID 6228DimethylformamideHCID 24386Thionyl ChlorideHCID 37805552,4-Difluoro-3-methoxybenzoic acid

Product 1

HCID 11543054Ethyl 2,4-difluoro-3-methoxybenzoate

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
60 °C

Procedure

2,4-Difluoro-3-methoxybenzoic acid (18.8 g) was placed in a reaction vessel and was suspended in 100 ml of toluene added thereto at room temperature. After dropwise addition of 0.5 mL of N,N-dimethylformamide, 14.6 mL of thionyl chloride was added dropwise, and the resulting mixture was heated to 60° C. with stirring. After 7 hours, 50 mL of ethanol was added and an insoluble matter was filtered out. The filtrate was washed with water and saturated brine, and dried with anhydrous sodium sulfate. The solvent was distilled away to give the title compound (21.4 g) as a pale yellow oil.

Workup

  1. additionadded
  2. customat room temperature
  3. additionwas added dropwise
  4. filtrationan insoluble matter was filtered out
  5. washThe filtrate was washed with water and saturated brine
  6. dry with materialdried with anhydrous sodium sulfate
  7. distillationThe solvent was distilled away

Sources & evidence

ORD record
ord-e7bc56c060554da4b46d4bb584f49f22
Source dataset
uspto-grants-2009_12
Patent number
US07626029B2

Reaction notes

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