Water → 1-(benzyloxy)-2-bromo-4-methylbenzene

HRID 1500466Notes

Reaction equation

HRID 1500466 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][C:3]=1[OH:9].C([O-])([O-])=O.[K+].[K+].[CH2:16](Br)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.O>CN(C=O)C>[CH2:16]([O:9][C:3]1[CH:4]=[CH:5][C:6]([CH3:8])=[CH:7][C:2]=1[Br:1])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 231092-Bromo-4-methylphenol

Product 1

HCID 107312131-(benzyloxy)-2-bromo-4-methylbenzene

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

To a mixture of 2-bromo-4-methylphenol (5.0 g, 27 mmol) and K2CO3 (7.4 g, 53 mmol) in DMF (20 mL) was added benzyl bromide (3.5 mL, 29 mmol) at ambient temperature. It was stirred at 70° C., for 12 h. The mixture was poured into water (50 mL), extracted with EtOAc (150 mL), washed with water, brine, dried and concentrated. The residue was purified by column chromatography on silica gel eluting with hexanes/EtOAc (10:1) to give the title compound (3a).

Workup

  1. extractionextracted with EtOAc (150 mL)
  2. washwashed with water, brine
  3. customdried
  4. concentrationconcentrated
  5. customThe residue was purified by column chromatography on silica gel eluting with hexanes/EtOAc (10:1)

Sources & evidence

ORD record
ord-90ed584ce3b04933bd20e57d8da5d3da
Source dataset
uspto-grants-2015_12
Patent number
US09206166B2

Reaction notes

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