Sodium Hydroxide → 4-Bromo-3-(methoxymethyl)benzoic acid

HRID 2410527Notes

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].FC1C(C)=C(C2C=CC(C(O)=O)=CC=2COC)C=CC=1.[OH-].[Na+]>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

Conditions

Temperature: 60 °C

Procedure

To a solution of methyl 4-bromo-3-(methoxymethyl)benzoate (Intermediate 1, Step 2, 7.0 g, 27.0 mmol) in EtOH (210 mL) was added a 5 N aqueous solution of NaOH (16 mL, 80.0 mmol). The resulting mixture was heated at 60° C. for 1 hour. The reaction mixture was cooled to RT and concentrated under vacuum. The residue was taken up with water and washed with EtOAc. The aqueous layer was then acidified with a 1N aqueous solution of HCl and extracted with EtOAc. The organic layer was dried (MgSO4) 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), 8.00 (m, 1H), 7.77 (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

temperatureThe reaction mixture was cooled to RT
concentrationconcentrated under vacuum
washwashed with EtOAc
extractionextracted with EtOAc
dry with materialThe organic layer was dried (MgSO4)
concentrationconcentrated under vacuum

Sources & evidence

ORD record: ord-eb321c184e8b4439808b6c4d6521dd98
Source dataset: uspto-grants-2014_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08815919B2

Reaction notes

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