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Acetic Acid → Methyl 3-bromo-5-fluoro-4-hydroxybenzoate

HRID 1475777
Notes
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Reaction equation

HRID 1475777 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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 4

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

Product 1

HCID 57467610Methyl 3-bromo-5-fluoro-4-hydroxybenzoate

Reagents, catalysts & solvents 3

HCID 962WaterSolvent
HCID 6344
Dichloromethane
Solvent
HCID 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-6ab37640d32249d3acd4262482870817
Source dataset
uspto-grants-2015_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09018383B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes