Acetic Acid → HCID 57467610, compound

HRID 1918366Notes

Reaction equation

HRID 1918366 reaction equation
[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[C:6]([F:11])[CH:5]=1.C(O)(=O)C.[Br:17]Br.[O-]S([O-])=O.[Na+].[Na+]>O.CC(=O)OCC.C(Cl)Cl>[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:5]=[C:6]([F:11])[C:7]([OH:10])=[C:8]([Br:17])[CH:9]=1

Participants

8

Reactant 4

HCID 176Acetic AcidHCID 24408BromineHCID 24437Sodium SulfiteHCID 7019368Methyl 3-fluoro-4-hydroxybenzoate

Product 1

HCID 57467610HCID 57467610, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

3.9 g of 3-fluoro-4-hydroxy-benzoic acid methyl ester were dissolved using 25 ml of acetic acid and 25 ml of DCM. The mixture was cooled to 0° C. and 1.4 ml bromine added slowly (30 minutes) at 0° C. Stirring was continued at room temperature for 18 h. Then, 200 ml of EA and a solution of 7.6 g Na2SO3 in 50 ml of water were added and the resulting mixture was stirred for 10 minutes at room temperature. The layers were separated, and the organic layer was washed using first 50 ml of water and second 50 ml of a saturated aqueous NaCl-solution. The organic layer was dried using MgSO4 and evaporated to yield 5.0 g of the title compound that was used without further purification.

Workup

  1. stirringthe resulting mixture was stirred for 10 minutes at room temperature
  2. customThe layers were separated
  3. washthe organic layer was washed
  4. customThe organic layer was dried
  5. customevaporated

Sources & evidence

ORD record
ord-dde2a06914b74a9b90ebe587b4b63032
Source dataset
uspto-grants-2013_12
Patent number
US08618304B2

Reaction notes

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