Benzyl Bromide → HCID 67486773, compound

HRID 883041Notes

Reaction equation

HRID 883041 reaction equation
O[C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([OH:12])[CH:11]=1)[C:5]([O:7][CH3:8])=[O:6].[CH2:13](Br)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>CN(C=O)C>[CH3:8][O:7][C:5](=[O:6])[C:4]1[CH:3]=[C:2]([CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:11]=[C:10]([OH:12])[CH:9]=1

Participants

4

Reactant 2

HCID 7498Benzyl BromideHCID 75076Methyl 3,5-Dihydroxybenzoate

Product 1

HCID 67486773HCID 67486773, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of methyl 3,5-dihydroxybenzoate (50 g, 297 mmol) in DMF (270 ml) is added under nitrogen K2CO3 (61.6 g, 446 mmol, 1.5 eq.). Then benzyl bromide (53 ml, 446 mmol, 1.5 eq.) is added dropwise at 0° C. and the reaction mixture is stirred at RT for 24 h. The reaction mixture is filtered over celite, DMF is evaporated, water (500 ml) added and the reaction mixture extracted with ethyl acetate (2×500 ml). The combined organic layer is washed with brine, dried over MgSO4 and the solvent removed in vacuo. The residue is purified by column chromatography (cyclohexane/ethyl acetate 100/00 to 95/05) to give a mixture of the desired product and the di-alkylated compound. This mixture is purified by column chromatography (cyclohexane/acetone 95/05 to 90/10) to give 17.7 g of the title compound as white powder (yield of 23%).

Workup

  1. filtrationThe reaction mixture is filtered over celite, DMF
  2. customis evaporated
  3. additionwater (500 ml) added
  4. extractionthe reaction mixture extracted with ethyl acetate (2×500 ml)
  5. washThe combined organic layer is washed with brine
  6. dry with materialdried over MgSO4
  7. customthe solvent removed in vacuo
  8. customThe residue is purified by column chromatography (cyclohexane/ethyl acetate 100/00 to 95/05)
  9. customto give

Sources & evidence

ORD record
ord-a1d1faaedefb4505926eb06590e57982
Source dataset
uspto-grants-2012_08
Patent number
US08236824B2

Reaction notes

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