Benzyl Bromide → Methyl 5-bromo-4-methyl-2-[(phenylmethyl)oxy]benzoate

HRID 2204678Notes

Reaction equation

HRID 2204678 reaction equation
C(=O)([O-])[O-].[K+].[K+].[CH2:7](Br)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[Br:15][C:16]1[C:17]([CH3:27])=[CH:18][C:19]([OH:26])=[C:20]([CH:25]=1)[C:21]([O:23][CH3:24])=[O:22].C(OCC)(=O)C>CN(C)C=O.O>[Br:15][C:16]1[C:17]([CH3:27])=[CH:18][C:19]([O:26][CH2:7][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[C:20]([CH:25]=1)[C:21]([O:23][CH3:24])=[O:22]

Participants

7

Reactant 4

HCID 7498Benzyl BromideHCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 11425090Methyl 5-bromo-2-hydroxy-4-methylbenzoate

Product 1

HCID 66611587Methyl 5-bromo-4-methyl-2-[(phenylmethyl)oxy]benzoate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

Potassium carbonate (0.85 g, 6.12 mmol) and benzyl bromide (0.53 ml, 4.49 mmol) were added to a solution of methyl 5-bromo-2-hydroxy-4-methylbenzoate (1 g, 4.08 mmol) in N,N-dimethylformamide (10 ml). The mixture was stirred at room temperature for 72 hours. Ethyl acetate (20 ml) and water (20 ml) were added and the organic layer separated, washed with water (3×10 ml), dried (MgSO4) and the solvent removed in vacuo. Purification by column chromatography (10% ethyl acetate/hexanes) yielded the title compound as an oil. 1.35 g.

Workup

  1. customthe organic layer separated
  2. washwashed with water (3×10 ml)
  3. dry with materialdried (MgSO4)
  4. customthe solvent removed in vacuo
  5. customPurification by column chromatography (10% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-f9e7f82abb2949a48019ce3f52f847f8
Source dataset
uspto-grants-2016_06
Patent number
US09365551B2

Reaction notes

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