Benzyl Bromide → HCID 21966699, compound

HRID 2212575Notes

Reaction equation

HRID 2212575 reaction equation
[Cl:1][CH2:2][CH2:3][CH2:4][C:5]([C:7]1[CH:12]=[CH:11][C:10]([OH:13])=[CH:9][CH:8]=1)=[O:6].[CH2:14](Br)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH2:14]([O:13][C:10]1[CH:9]=[CH:8][C:7]([C:5](=[O:6])[CH2:4][CH2:3][CH2:2][Cl:1])=[CH:12][CH:11]=1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 815784-Chloro-4'-hydroxybutyrophenone

Product 1

HCID 21966699HCID 21966699, compoundYield 35%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

4-Chloro-1-(4-hydroxy-phenyl)-butan-1-one (1.0 g, 5.03 mmol) and benzyl bromide (0.86 g, 5.03 mmol) were combined with potassium carbonate (2 g) in acetone (50 mL). The reaction was stirred over 2 days at room temperature and became a thick slurry. This was partitioned between ethyl acetate and water saturated KH2PO4. The organic layer was washed with brine, dried over magnesium sulfate, and concentrated to give a semi-solid. The product was purified by FCC on silica gel eluting hexane:ethyl acetate (80:20, v:v) to give 1-(4-benzyloxy-phenyl)-4-chloro-butan-1-one (0.5 g, 35%) as a solid. MS found: (M+H)+=289.

Workup

  1. customThis was partitioned between ethyl acetate and water saturated KH2PO4
  2. washThe organic layer was washed with brine
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated
  5. customto give a semi-solid
  6. customThe product was purified by FCC on silica gel
  7. washeluting hexane:ethyl acetate (80:20, v:v)

Sources & evidence

ORD record
ord-a75dc6642e15460db9b7400528d71080
Source dataset
uspto-grants-2006_09
Patent number
US07102008B2

Reaction notes

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