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

HRID 1630964Notes

Reaction equation

HRID 1630964 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 (37.5 g, 122 mmol) in MeOH (1.1 L) 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% aqueous solution of NaHCO3 (200 mL) and brine (200 mL), dried (MgSO4) and concentrated affording the title compound as a beige solid (29.8 g, 94%). HPLC (Method A), Rt 4.4 min (purity: 93.0%). UPLC/MS, M−(ESI): 227.2. 1H NMR (DMSO-d6, 300 MHz) δ 8.06 (m, 1H), 7.83 (m, 2H), 4.54 (m, 2H), 3.90 (s, 3H), 3.45 (s, 3H).

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% aqueous solution of NaHCO3 (200 mL) and brine (200 mL)
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-2e77b522d6ec4f6489fc88bde6662686
Source dataset
uspto-grants-2014_07
Patent number
US08791142B2

Reaction notes

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