3-Bromobenzaldehyde → HCID 2757099, compound

HRID 2060776Notes

Reaction equation

HRID 2060776 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH:5]=[O:6].[CH2:10]([Mg]Br)[CH:11]=[CH2:12]>C(OCC)C>[Br:1][C:2]1[CH:3]=[C:4]([CH:5]([OH:6])[CH2:12][CH:11]=[CH2:10])[CH:7]=[CH:8][CH:9]=1

Participants

4

Reactant 2

HCID 765833-BromobenzaldehydeHCID 178455850HCID 178455850, compound

Product 1

HCID 2757099HCID 2757099, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

To a solution of 3-bromobenzaldehyde (15.8 g, 85.6 mmol) in dry diethyl ether (200 mL) at 0° C. under nitrogen atmosphere with stirring is added allylmagnesium bromide solution in ether (85.6 mL, 85.6 mmol) dropwise. The resulting mixture is warmed to room temperature over 1 hr and is quenched by the addition of 1 N HCl aqueous solution. The reaction is extracted with dichloromethane, washed with brine, dried over sodium sulfate, filtered, and concentrated under reduced pressure. The crude product is purified by silica gel chromatography eluting with 0% to 100% dichloromethane in hexanes over 50 minutes to give the title compound as a racemic mixture (17.01 g, 88%). ES/MS m/e (79Br/81Br) 227, 229 (M+1).

Workup

  1. customis quenched by the addition of 1 N HCl aqueous solution
  2. extractionThe reaction is extracted with dichloromethane
  3. washwashed with brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe crude product is purified by silica gel chromatography
  8. washeluting with 0% to 100% dichloromethane in hexanes over 50 minutes

Sources & evidence

ORD record
ord-8f1a496d89d84ade96d53019ead090ad
Source dataset
uspto-grants-2012_10
Patent number
US08278441B2

Reaction notes

Loading…