Hydrogen Bromide → 2-Fluoro-5-hydroxy-4-methylbenzoic acid

HRID 446274Notes

Reaction equation

HRID 446274 reaction equation
[F:1][C:2]1[CH:10]=[C:9]([CH3:11])[C:8]([O:12]C)=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].Br>C(O)(=O)C>[F:1][C:2]1[CH:10]=[C:9]([CH3:11])[C:8]([OH:12])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5]

Participants

4

Reactant 2

HCID 260Hydrogen BromideHCID 669701962-Fluoro-5-methoxy-4-methylbenzoic acid

Product 1

HCID 583969752-Fluoro-5-hydroxy-4-methylbenzoic acid

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
140 °C

Procedure

To 2-fluoro-5-methoxy-4-methylbenzoic acid (650 mg, 3.53 mmol) was added 49% aqueous HBr (6.5 mL) and glacial acetic acid (5.5 mL). The mixture was heated overnight at 140° C., cooled to RT, diluted with ice water and extracted with EtOAc. The organic layer was dried over Na2SO4, filtered and concentrated to yield 2-fluoro-5-hydroxy-4-methylbenzoic acid. MS m/z=171 [M+1]+. Calc'd for C8H7FO3: 170.20.

Workup

  1. temperaturecooled to RT
  2. extractionextracted with EtOAc
  3. dry with materialThe organic layer was dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-2a4326ae52834f2b9256d97e36674e0e
Source dataset
uspto-grants-2013_07
Patent number
US08476434B2

Reaction notes

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