Hydrochloric Acid → Methyl 4-bromo-2,6-difluorobenzoate

HRID 1925004Notes

Reaction equation

HRID 1925004 reaction equation
[Br:1][C:2]1[CH:10]=[C:9]([F:11])[C:5]([C:6]([OH:8])=[O:7])=[C:4]([F:12])[CH:3]=1.S(Cl)(Cl)=O.[CH3:17]N(C=O)C.Cl>C(Cl)Cl.CO>[CH3:17][O:7][C:6](=[O:8])[C:5]1[C:4]([F:12])=[CH:3][C:2]([Br:1])=[CH:10][C:9]=1[F:11]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 6228DimethylformamideHCID 24386Thionyl ChlorideHCID 27732984-Bromo-2,6-difluorobenzoic acid

Product 1

HCID 26343953Methyl 4-bromo-2,6-difluorobenzoate

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

To a suspension of 4-Bromo-2,6-difluoro-benzoic acid (5 g, 21 mmol) in DCM (10 mL) is added thionyl chloride (15 mL) and DMF (0.5 mL). The mixture is stirred at room temperature for 2.5 h. It is then cooled to 0° C. and MeOH (20 mL) is added carefully causing vigorous HCl evolution. After stirring for an additional 0.5 h, the clear solution is partitioned between DCM (50 mL) and water (50 mL). The organic layer is washed with saturated NaHCO3, brine, dried over MgSO4 and the solvent is removed under vacuum to afford the title compound as a pale yellow oil which is used without further purification.

Workup

  1. temperatureIt is then cooled to 0° C.
  2. stirringAfter stirring for an additional 0.5 h
  3. customthe clear solution is partitioned between DCM (50 mL) and water (50 mL)
  4. washThe organic layer is washed with saturated NaHCO3, brine
  5. dry with materialdried over MgSO4
  6. customthe solvent is removed under vacuum

Sources & evidence

ORD record
ord-74db4ad884e84be295fe9136d48880ad
Source dataset
uspto-grants-2012_05
Patent number
US08178530B2

Reaction notes

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