Benzyl Bromide → HCID 66759590, compound

HRID 880372Notes

Reaction equation

HRID 880372 reaction equation
[OH:1][C:2]1[CH:7]=[C:6]([O:8][CH2:9][O:10][CH2:11][CH2:12][O:13][CH3:14])[CH:5]=[C:4]([O:15][CH2:16][O:17][CH2:18][CH2:19][O:20][CH3:21])[C:3]=1[C:22](=[O:24])[CH3:23].C(=O)([O-])[O-].[K+].[K+].[CH2:31](Br)[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1>CN(C=O)C.C(OCC)(=O)C>[CH2:31]([O:1][C:2]1[CH:7]=[C:6]([O:8][CH2:9][O:10][CH2:11][CH2:12][O:13][CH3:14])[CH:5]=[C:4]([O:15][CH2:16][O:17][CH2:18][CH2:19][O:20][CH3:21])[C:3]=1[C:22](=[O:24])[CH3:23])[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1

Participants

6

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 12044953HCID 12044953, compound

Product 1

HCID 66759590HCID 66759590, compoundYield 73%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a stirred suspension of 1-{2-hydroxy-4,6-bis[(2-methoxyethoxy)methoxy]phenyl}ethanone (3.53 g, 10 mmol), potassium carbonate (1.7 g, 14 mmol) in DMF (15 mL) was added benzylbromide (2.1 g, 12 mmol). After stirring overnight, the reaction mixture was diluted with ethyl acetate (100 mL) and thoroughly washed with brine. The organic phase was dried and evaporated to dryness. The crude was chromatographed on a small pad of silica gel eluting with hexane/ethyl acetate 7/1, to provide the title compound (g 3.25, yield 73%).

Workup

  1. washthoroughly washed with brine
  2. customThe organic phase was dried
  3. customevaporated to dryness
  4. customThe crude was chromatographed on a small pad of silica gel eluting with hexane/ethyl acetate 7/1

Sources & evidence

ORD record
ord-fe3708ca49c9477c8b65b08982ea5648
Source dataset
uspto-grants-2015_03
Patent number
US08993556B2

Reaction notes

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