Methanol → Methyl 2-(3-(bromomethyl)-4-methoxyphenyl)acetate

HRID 2387883Notes

Reaction equation

HRID 2387883 reaction equation
S(Cl)(Cl)=O.[Br:5][CH2:6][C:7]1[CH:8]=[C:9]([CH2:15][C:16]([OH:18])=[O:17])[CH:10]=[CH:11][C:12]=1[O:13][CH3:14].[CH3:19]O>>[Br:5][CH2:6][C:7]1[CH:8]=[C:9]([CH2:15][C:16]([O:18][CH3:19])=[O:17])[CH:10]=[CH:11][C:12]=1[O:13][CH3:14]

Participants

4

Reactant 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 671652482-(3-(Bromomethyl)-4-methoxyphenyl)acetic acid

Product 1

HCID 68416244Methyl 2-(3-(bromomethyl)-4-methoxyphenyl)acetate

Conditions

Temperature
0 °C

Procedure

Thionyl chloride (1.359 ml) was added dropwise to a solution of the product from step (i) (4.02 g) in MeOH (50 mL), the resulting suspension was stirred at 0° C. for 10 min then warmed to rt for 18 h. The solvent was evaporated and the residue was diluted with EtOAc washed with sat. NaHCO3 and sat. brine. The organic phase was dried, filtered and evaporated. The crude product was purified by chromatography, to give the subtitle compound as a yellow oil, 1.47 g.

Workup

  1. temperaturethen warmed to rt for 18 h
  2. customThe solvent was evaporated
  3. additionthe residue was diluted with EtOAc
  4. washwashed with sat. NaHCO3 and sat. brine
  5. customThe organic phase was dried
  6. filtrationfiltered
  7. customevaporated
  8. customThe crude product was purified by chromatography

Sources & evidence

ORD record
ord-7ef4947e0cf749b98f9de5da2d874fc6
Source dataset
uspto-grants-2012_09
Patent number
US08268990B2

Reaction notes

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