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

HRID 73328Notes

Reaction equation

HRID 73328 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-55f5383bdd8641a99ef7dbbbdbd429e8
Source dataset
uspto-grants-2014_09
Patent number
US08829040B2

Reaction notes

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