Benzenepropanal → 2-Bromo-3-phenylpropanal

HRID 408484Notes

Reaction equation

HRID 408484 reaction equation
[Br:1]Br.[C:3]1([CH2:9][CH2:10][CH:11]=[O:12])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.C(=O)(O)[O-].[Na+]>ClCCl>[Br:1][CH:10]([CH2:9][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1)[CH:11]=[O:12]

Participants

5

Reactant 3

HCID 7707BenzenepropanalHCID 24408BromineHCID 516892Sodium Bicarbonate

Product 1

HCID 113902282-Bromo-3-phenylpropanalYield 70.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of bromine (15.2 g, 95.1 mmol) in 30 mL of dichloromethane was added to a solution of 3-phenyl-propionaldehyde (13.4 g, 100 mmol) in dichloromethane (150 mL) at 0° C. over 20 minutes. The reaction mixture was allowed to stir for 2 hours and then a saturated aqueous solution of sodium bicarbonate (100 mL) was added to the mixture. The organic layer was separated and the aqueous layer was washed with dichloromethane (50 mL). The combined organic layers were washed with water, a saturated aqueous solution of sodium chloride, and then evaporated to dryness to give an orange oil (14.2 g), which was used directly in the next step.

Workup

  1. customThe organic layer was separated
  2. washthe aqueous layer was washed with dichloromethane (50 mL)
  3. washThe combined organic layers were washed with water
  4. customa saturated aqueous solution of sodium chloride, and then evaporated to dryness

Sources & evidence

ORD record
ord-ad1c5be33b5148d7992c435e36361bb9
Source dataset
uspto-grants-2014_06
Patent number
US08759335B2

Reaction notes

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