Water → 4-Bromo-3-(methoxymethyl)benzoic acid

HRID 219828Notes

Reaction equation

HRID 219828 reaction equation
[Br:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8]C)=[O:7])=[CH:4][C:3]=1[CH2:12][O:13][CH3:14].COCC1C=C(C(O)=O)C=CC=1C1C=CC=CC=1C.[OH-].[Na+].O>CCO>[Br:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([OH:8])=[O:7])=[CH:4][C:3]=1[CH2:12][O:13][CH3:14]

Participants

6

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 58554220Methyl 4-bromo-3-(methoxymethyl)benzoateHCID 594958222-(Methoxymethyl)-2'-methylbiphenyl-4-carboxylic acid

Product 1

HCID 197712294-Bromo-3-(methoxymethyl)benzoic acidYield 87%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of methyl 4-bromo-3-(methoxymethyl)benzoate (Intermediate 28, step 2), (7 g; 27.02 mmol) in EtOH (210 mL) was added NaOH (16.21 mL; 5 M; 81.05 mmol). The resulting reaction mixture was heated at 60° C. for one hour. It was then cooled to RT and concentrated under vacuum to give a yellow solid. Water was added and the aqueous phase was washed with EtOAc. The aqueous phase was then acidified with HCl (1 M) and extracted with EtOAc. Organic phase was dried over MgSO4, filtered and concentrated under vacuum to give the title compound as a yellow solid (5.81 g, 87%). 1H NMR (DMSO-d6, 300 MHz) 13.19 (br s, 1H), 8 (m, 1H), 7.77-7.76 (m, 2H), 4.49 (s, 2H), 3.40 (s, 3H). LC/MS (Method B): 245.0 (M−H)−. HPLC (Method A) Rt 3.63 min (purity: 97.4%).

Workup

  1. customThe resulting reaction mixture
  2. temperatureIt was then cooled to RT
  3. concentrationconcentrated under vacuum
  4. customto give a yellow solid
  5. washthe aqueous phase was washed with EtOAc
  6. extractionextracted with EtOAc
  7. dry with materialOrganic phase was dried over MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-6f0916ade3be472ca95e0c1d081af041
Source dataset
uspto-grants-2012_06
Patent number
US08202865B2

Reaction notes

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