Hydrogen Bromide → 2-Fluoro-5-hydroxybenzoic acid

HRID 70003

Reaction equation

HRID 70003 reaction equation
[F:1][C:2]1[CH:10]=[CH:9][C:8]([O:11]C)=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].Br>C(O)(=O)C>[F:1][C:2]1[CH:10]=[CH:9][C:8]([OH:11])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5]

Participants

4

Reactant 2

HCID 260Hydrogen BromideHCID 27745432-Fluoro-5-methoxybenzoic acid

Product 1

HCID 27744802-Fluoro-5-hydroxybenzoic acid

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
140 °C

Procedure

To 2-fluoro-5-methoxybenzoic acid (5.00 g, 29.4 mmol) was added 49% aqueous HBr (50 mL) and glacial acetic acid (40 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-hydroxybenzoic acid. MS m/z=157 [M+1]+. Calc'd for C7H5FO3: 156.11.

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-0d749d0deff54f41803cec83004fd625
Source dataset
uspto-grants-2014_09
Patent number
US08822514B2

Linked notes

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