1,2-Dichloroethane → 4-Bromo-2-fluoro-benzoic acid methyl ester

HRID 2102928Notes

Reaction equation

HRID 2102928 reaction equation
[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[C:4]([F:11])[CH:3]=1.Cl[CH2:13]CCl.S(Cl)(Cl)=O.CN(C=O)C>CO>[CH3:13][O:7][C:6](=[O:8])[C:5]1[CH:9]=[CH:10][C:2]([Br:1])=[CH:3][C:4]=1[F:11]

Participants

6

Reactant 4

HCID 111,2-Dichloroethane2×HCID 6228DimethylformamideHCID 24386Thionyl Chloride2×HCID 3026814-Bromo-2-fluorobenzoic acid

Product 1

HCID 113453114-Bromo-2-fluoro-benzoic acid methyl ester

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

4-Bromo-2-fluorobenzoic acid (10 g, 0.04 mol) was suspended in 1,2-dichloroethane (60 mL, 0.8 mol) to which was added thionyl chloride (10 mL, 0.1 mol) followed by a drop of DMF. The mixture was heated to reflux for 1 hour. Excess thionyl chloride and 1,2-dichloroethane were stripped off and the crude product was treated with methanol (50 mL) and heated to reflux for an hour. The mixture was concentrated to dryness, dissolved in dichloromethane, treated with cold sat. sodium bicarbonate solution. The organic layer was dried, then concentrated under vacuum to obtain the title compound as a white solid.

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 1 hour
  3. temperatureheated
  4. temperatureto reflux for an hour
  5. concentrationThe mixture was concentrated to dryness
  6. dissolutiondissolved in dichloromethane
  7. additiontreated with cold sat. sodium bicarbonate solution
  8. customThe organic layer was dried
  9. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-bc331b4a94b047a1a989fba7dc451eba
Source dataset
uspto-grants-2009_08
Patent number
US07576099B2

Reaction notes

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