Benzyl Bromide → 2-(Benzyloxy)-5-bromobenzaldehyde

HRID 392918Notes

Reaction equation

HRID 392918 reaction equation
[CH2:1](Br)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-].[Cs+].[Cs+].[OH:15][C:16]1[CH:23]=[CH:22][C:21]([Br:24])=[CH:20][C:17]=1[CH:18]=[O:19]>CN(C=O)C.O>[CH2:1]([O:15][C:16]1[CH:23]=[CH:22][C:21]([Br:24])=[CH:20][C:17]=1[CH:18]=[O:19])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 7498Benzyl BromideHCID 10796Cesium carbonateHCID 728635-Bromosalicylaldehyde

Product 1

HCID 7330872-(Benzyloxy)-5-bromobenzaldehydeYield 92.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

Benzyl bromide (18 mL, 14.9 mmol) and cesium carbonate (8.1 g, 24.9 mmol) were added to a solution of 2-hydroxy-5-bromo benzaldehyde 2 g, 9.95 mmol) in anhydrous DMF (25 mL) at room temperature. The reaction was heated to 80° C. for two hours, cooled and diluted with water (50 mL). The mixture was extracted with ethyl acetate (3×40 mL) and the combined organic layers were washed with water (1×50 mL) and brine (1×50 mL), dried (Na2SO4), filtered and concentrated. The residue was purified by flash chromatography (10% ethyl acetate/hexane) to afford 2.67 g of the title compound as a colorless oil (92%). MS: 291 (M+H)+. 1H NMR (400 MHz, CDCl3) δ 7.94 (s, 1H); 7.6 (dd, 1H, J=8.9, 2.7 Hz); 7.39 (m, 6H); 6.92 (d, 1H, J=8.9 Hz); 5.18 (s, 2H).

Workup

  1. temperaturecooled
  2. extractionThe mixture was extracted with ethyl acetate (3×40 mL)
  3. washthe combined organic layers were washed with water (1×50 mL) and brine (1×50 mL)
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by flash chromatography (10% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-1ac2352c59034142b451751306c27019
Source dataset
uspto-grants-2004_10
Patent number
US06803457B1

Reaction notes

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