Methanol → Methyl 4-bromo-3-(methoxymethyl)benzoate

HRID 219808Notes

Reaction equation

HRID 219808 reaction equation
[Br:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][C:3]=1[CH2:12]Br.[CH3:14][OH:15]>>[Br:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][C:3]=1[CH2:12][O:15][CH3:14]

Participants

3

Reactant 2

HCID 887MethanolHCID 11460987Methyl 4-Bromo-3-(bromomethyl)benzoate

Product 1

HCID 58554220Methyl 4-bromo-3-(methoxymethyl)benzoateYield 94%

Procedure

A solution of methyl 4-bromo-3-(bromomethyl)benzoate (37.50 g; 121.77 mmol; 1 eq.) in MeOH (1 125 mL) was refluxed for 4 days. After concentration, the mixture was partitioned between EtOAc (500 mL) and water (200 mL). The organic layer was washed with a 5% NaHCO3 aqueous solution (200 mL), brine (200 mL), dried over MgSO4 and concentrated affording the title compound as a beige solid (29.8 g, 94%). 1H NMR (DMSO-d6, 300 MHz) δ 8.06-8.05 (m, 1H), 7.83 (d, J=1.23 Hz, 2H), 4.54 (m, 2H), 3.90 (s, 3H), 3.45 (s, 3H). LC/MS (Method B): 227.2 (M−H)−. HPLC (Method A) Rt 4.42 min (Purity: 93.0%).

Workup

  1. concentrationAfter concentration
  2. customthe mixture was partitioned between EtOAc (500 mL) and water (200 mL)
  3. washThe organic layer was washed with a 5% NaHCO3 aqueous solution (200 mL), brine (200 mL)
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-88b74c7e56ef48a2a4f943a189275c7a
Source dataset
uspto-grants-2012_06
Patent number
US08202865B2

Reaction notes

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