Benzyl Bromide → HCID 66726186, compound

HRID 572486Notes

Reaction equation

HRID 572486 reaction equation
[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[C:8]([OH:10])[CH:7]=[CH:6][C:5]=1[Br:11].C([O-])([O-])=O.[K+].[K+].[CH:19]1[CH:24]=[CH:23][C:22]([CH2:25]Br)=[CH:21][CH:20]=1.CC(=O)OCC>CN(C=O)C.O>[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[C:8]([O:10][CH2:25][C:22]2[CH:23]=[CH:24][CH:19]=[CH:20][CH:21]=2)[CH:7]=[CH:6][C:5]=1[Br:11]

Participants

7

Reactant 4

HCID 7498Benzyl BromideHCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 189336882-broMo-5-hydroxybenzoic acid Methyl ester

Product 1

HCID 66726186HCID 66726186, compoundYield 90%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-Bromo-5-hydroxy-benzoic acid methyl ester (80 g, 347 mmol) and K2CO3 (71.9 g, 520 mmol) in DMF (800 mL) was added BnBr (500 g, 416.2 mmol) at RT. The mixture was stirred at RT under N2 for 5 hr. The reaction mixture was diluted with H2O (500 mL) and extracted with ethyl acetate (100 mL*3). The organic phase was washed with saturated sodium bicarbonate solution 500 mL, dried over Na2SO4. After concentration, the crude product was purified by silica gel chromatography eluted with PE:EA=4:1 to give title product (100 g, 90% yield) as an off-white solid.

Workup

  1. extractionextracted with ethyl acetate (100 mL*3)
  2. washThe organic phase was washed with saturated sodium bicarbonate solution 500 mL
  3. dry with materialdried over Na2SO4
  4. concentrationAfter concentration
  5. customthe crude product was purified by silica gel chromatography
  6. washeluted with PE

Sources & evidence

ORD record
ord-f2247b69238945d7bc0efcd84dca348c
Source dataset
uspto-grants-2015_05
Patent number
US09029391B2

Reaction notes

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