Methanol → 5-Benzyloxy-2-bromo-4-methylbenzaldehyde

HRID 1674573Notes

Reaction equation

HRID 1674573 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH:14]=[CH:15][C:16]=1[CH3:17])[CH:12]=[O:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CO.[Br:20]Br.O>ClCCl>[CH2:1]([O:8][C:9]1[C:16]([CH3:17])=[CH:15][C:14]([Br:20])=[C:11]([CH:10]=1)[CH:12]=[O:13])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 962WaterHCID 24408BromineHCID 161013893-(Benzyloxy)-4-methylbenzaldehyde

Product 1

HCID 206315825-Benzyloxy-2-bromo-4-methylbenzaldehydeYield 74.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 3-benzyloxy-4-methylbenzaldehyde (0.39 g) in a mixed solvent of dichloromethane (1 mL) and methanol (1 mL) was added a solution of bromine (0.410 g) in dichloromethane (0.2 mL) at 0° C. and this mixture was stirred at room temperature for 2 hours. This mixture was poured into water and the resulting mixture was extracted with dichloromethane. The organic layer was washed with brine, and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure. The residue was purified by column chromatography on silica gel (eluent: n-hexane/ethyl acetate) to give the title compound (0.39 g).

Workup

  1. extractionthe resulting mixture was extracted with dichloromethane
  2. washThe organic layer was washed with brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was removed under reduced pressure
  5. customThe residue was purified by column chromatography on silica gel (eluent: n-hexane/ethyl acetate)

Sources & evidence

ORD record
ord-180632f1fad94813b24d3ea1e29f128f
Source dataset
uspto-grants-2011_08
Patent number
US08003647B2

Reaction notes

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