Benzyl Bromide → HCID 90015050, compound

HRID 1053848Notes

Reaction equation

HRID 1053848 reaction equation
[C:1]([C:4]1[CH:5]=[C:6]([CH:10]=[CH:11][CH:12]=1)[C:7]([OH:9])=[O:8])(=[O:3])[CH3:2].C([O-])([O-])=O.[Na+].[Na+].[CH2:19](Br)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>CN(C=O)C.CCOC(C)=O>[C:1]([C:4]1[CH:5]=[C:6]([CH:10]=[CH:11][CH:12]=1)[C:7]([O:9][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[O:8])(=[O:3])[CH3:2]

Participants

6

Reactant 3

HCID 7498Benzyl BromideHCID 10340Sodium CarbonateHCID 2203243-Acetylbenzoic acid

Product 1

HCID 90015050HCID 90015050, compoundYield 84%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 3-acetylbenzoic acid (6.00 g, 0.36 mol) in DMF (36 mL) was added Na2CO3 (4.26 g, 0.40 mol) at 0° C. and the reaction stirred for 10 min. After 10 min, benzyl bromide (4.80 mL, 0.40 mol) was added and the reaction stirred at room temperature for 1 h. The reaction mixture was diluted with EtOAc (100 mL) and washed with H2O (50 mL) and brine (50 mL), dried over Na2SO4, filtered and concentrated. The residue was purified by combiflash chromatography (silica gel, 40 g, 2-5% ethyl acetate/hexanes) to afford the title compound (7.73 g, 84%) as a white solid.

Workup

  1. waitAfter 10 min
  2. stirringthe reaction stirred at room temperature for 1 h
  3. washwashed with H2O (50 mL) and brine (50 mL)
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by combiflash chromatography (silica gel, 40 g, 2-5% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-6639ab3b9ca74c31aa9c06f29e1521af
Source dataset
uspto-grants-2016_07
Patent number
US09394250B2

Reaction notes

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