4-Bromobenzaldehyde → HCID 5151110, compound

HRID 1586236Notes

Reaction equation

HRID 1586236 reaction equation
[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=O)=[CH:4][CH:3]=1.C1(P(=[CH:29][CH:30]=[O:31])(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C(Cl)Cl>[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[CH:29][CH:30]=[O:31])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 707414-BromobenzaldehydeHCID 75051(Triphenylphosphoranylidene)acetaldehyde

Product 1

HCID 5151110HCID 5151110, compoundYield 35.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Part A. 4-bromobenzaldehyde (9.11 gm, 49.28 mmol) and (triphenylphosphoranylidene) acetaldehyde (15.00 gm, 49.28 mmol) were combined in 250 mL of methylene chloride and stirred overnight at room temperature. The volatiles were removed under vacuum and the residue dissolved in 200 mL of EtOAc, filtered through a pad of silica gel and concentrated to dryness. The resulting residue was purified by flash chromatography on silica gel eluting hexane:ethyl acetate (3:1, v:v) to give 3-(4-bromophenyl) acrolein as a pale yellow solid 3.67 gm, (35%). MS m/e 211 (M+H)+ 1 H NMR (CDCl3) 6.70 (dd, 1H), 7.43 (m, 3H), 7.54 (d, 2H), 9.69 (d, 1H).

Workup

  1. customThe volatiles were removed under vacuum
  2. dissolutionthe residue dissolved in 200 mL of EtOAc
  3. filtrationfiltered through a pad of silica gel
  4. concentrationconcentrated to dryness
  5. customThe resulting residue was purified by flash chromatography on silica gel
  6. washeluting hexane:ethyl acetate (3:1, v:v)

Sources & evidence

ORD record
ord-5262caeffb054c2ca1be9aa1380f6067
Source dataset
uspto-grants-1999_08
Patent number
US05942544

Reaction notes

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