Benzyl Bromide → HCID 21931457, compound

HRID 1244151Notes

Reaction equation

HRID 1244151 reaction equation
[CH3:1][C:2]([C:4]1[CH:9]=[C:8]([Br:10])[C:7]([OH:11])=[C:6]([Br:12])[CH:5]=1)=[O:3].C([O-])([O-])=O.[K+].[K+].[CH2:19](Br)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>CN(C=O)C.O>[CH2:19]([O:11][C:7]1[C:6]([Br:12])=[CH:5][C:4]([C:2](=[O:3])[CH3:1])=[CH:9][C:8]=1[Br:10])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

6

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 761581-(3,5-Dibromo-4-hydroxyphenyl)ethan-1-one

Product 1

HCID 21931457HCID 21931457, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 3,5-dibromo-4-hydroxyacetophenone from Example 45A (15 g, 51.2 mmol) in DMF (51 mL) was added K2CO3 (10.2 g, 74.1 mmol) and benzyl bromide (6.0 mL, 50.7 mmol). The reaction stirred at room temperature for 45 minutes. It was diluted with water (200 mL) and extracted with EtOAc (3×75 mL). The combined organic layers were washed with 2M NaOH solution (2×75 mL), water (75 mL), and brine (75 mL) and then dried over MgSO4 and concentrated in vacuo to give 1-(4-benzyloxy-3,5-dibromo-phenyl)-ethanone as an off white solid (14.3 g, 37.2 mmol, 73% yield).

Workup

  1. extractionextracted with EtOAc (3×75 mL)
  2. washThe combined organic layers were washed with 2M NaOH solution (2×75 mL), water (75 mL), and brine (75 mL)
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-c56a7da258c9463799da70d9e8e77692
Source dataset
uspto-grants-2006_10
Patent number
US07119205B2

Reaction notes

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