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

HRID 1635041Notes

Reaction equation

HRID 1635041 reaction equation
[Br:1][C:2]1[CH:9]=[C:6]([CH:7]=[O:8])[C:5]([OH:10])=[CH:4][CH:3]=1.[CH2:11](Br)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.O>[CH2:11]([O:10][C:5]1[CH:4]=[CH:3][C:2]([Br:1])=[CH:9][C:6]=1[CH:7]=[O:8])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

6

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 728635-Bromosalicylaldehyde

Product 1

HCID 7330872-(Benzyloxy)-5-bromobenzaldehyde

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To 5-bromosalicylaldehyde (24) (10.01 g, 49.8 mmol) in DMF (50 mL) were added benzyl bromide (6.5 mL, 54.6 mmol) and potassium carbonate (13.76 g, 99.6 mmol). The reaction mixture was stirred at room temperature for 72 hours. The solution was diluted with water, and extracted with ethyl acetate (3×200 mL). The combined organic extracts were washed with brine (2×100 mL), dried with magnesium sulfate, filtered, evaporated in vacuo, and dried under high vacuum. The product (25) was crystallized from ethyl acetate in hexane to give 10.96 g (76%) as a white solid.

Workup

  1. extractionextracted with ethyl acetate (3×200 mL)
  2. washThe combined organic extracts were washed with brine (2×100 mL)
  3. dry with materialdried with magnesium sulfate
  4. filtrationfiltered
  5. customevaporated in vacuo
  6. customdried under high vacuum
  7. customThe product (25) was crystallized from ethyl acetate in hexane
  8. customto give 10.96 g (76%) as a white solid

Sources & evidence

ORD record
ord-536f2595be5a4aae81bad9151b160c60
Source dataset
uspto-grants-2003_01
Patent number
US06509335B1

Reaction notes

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