Benzyl Bromide → Benzyl 2-(3,4-dimethoxyphenyl)-2-hydroxyacetate

HRID 1438177Notes

Reaction equation

HRID 1438177 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:11]([OH:15])[C:12]([OH:14])=[O:13])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].C(=O)([O-])[O-].[Cs+].[Cs+].[CH2:22](Br)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>CN(C=O)C.O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:11]([OH:15])[C:12]([O:14][CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[O:13])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10]

Participants

6

Reactant 3

HCID 7498Benzyl BromideHCID 10796Cesium carbonateHCID 138548502-(3,4-Dimethoxyphenyl)-2-hydroxyacetic acid

Product 1

HCID 57448185Benzyl 2-(3,4-dimethoxyphenyl)-2-hydroxyacetateYield 44.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To 137C (830 mg, 3.9 mmol) in DMF (15 mL) was added cesium carbonate (2.6 g, 8.0 mmol) followed by benzyl bromide (0.6 mL, 5 mmol). After stirring at rt overnight, the reaction was diluted with water, and was extracted with ethyl acetate (2×30 mL). The organic layer was washed with brine, dried (Na2SO4), filtered and concentrated. The resulting residue was purified via silica gel chromatography (0-40% ethyl acetate/hexanes) to provide 137D (520 mg, 44%). LC-MS: 445.31 (M+H)+.

Workup

  1. extractionwas extracted with ethyl acetate (2×30 mL)
  2. washThe organic layer was washed with brine
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe resulting residue was purified via silica gel chromatography (0-40% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-b90a22d2eef142a7a93f270469265176
Source dataset
uspto-grants-2009_11
Patent number
US07622585B2

Reaction notes

Loading…