Hydrochloric Acid → 3-Bromo-4-(hydroxymethyl)benzoic acid

HRID 594069Notes

Reaction equation

HRID 594069 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[CH2:11]Br)[C:5]([OH:7])=[O:6].Cl.[OH2:14]>CCOC(C)=O>[Br:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[CH2:11][OH:14])[C:5]([OH:7])=[O:6]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 116163143-bromo-4-(bromomethyl)benzoic Acid

Product 1

HCID 196884153-Bromo-4-(hydroxymethyl)benzoic acid

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
95 °C

Procedure

To a solution of yield 3-bromo-4-(bromomethyl)benzoic acid (1.0 equiv.) in Water (0.56 M) at 95° C. was added potassium carbonate K2CO3 (5.0 equiv.). The homogenous reaction mixture was stirred at 95° C. in an oil bath for 1 hr. The reaction mixture was COOLED OFF TO RT, neutralized with 6 M HCl. diluted with EtOAc and washed with brine. The organic layer was dried over Na2SO4, filtered and concentrated. The crude was used in next step. LC/MS (m/z)=294.8 (MH+), Rt=0.80 min.

Workup

  1. temperatureThe reaction mixture was COOLED OFF TO RT
  2. washwashed with brine
  3. dry with materialThe organic layer was dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-2ce244944b804f83b89469331bd59216
Source dataset
uspto-grants-2016_01
Patent number
US09242969B2

Reaction notes

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