3-Bromobenzaldehyde → 5-(3-Bromophenyl)-4-pentenoic acid

HRID 2402382Notes

Reaction equation

HRID 2402382 reaction equation
[Br-].[C:2]([CH2:5][CH2:6][CH2:7][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)([OH:4])=[O:3].CC([O-])(C)C.[K+].[Br:33][C:34]1[CH:35]=[C:36]([CH:39]=[CH:40][CH:41]=1)[CH:37]=O>CS(C)=O.O>[Br:33][C:34]1[CH:35]=[C:36]([CH:37]=[CH:7][CH2:6][CH2:5][C:2]([OH:4])=[O:3])[CH:39]=[CH:40][CH:41]=1

Participants

6

Reactant 3

HCID 765833-BromobenzaldehydeHCID 10717451(3-Carboxypropyl)(triphenyl)phosphanium bromideHCID 23665647Potassium tert-butoxide

Product 1

HCID 667283885-(3-Bromophenyl)-4-pentenoic acidYield 38%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolvent2×HCID 962WaterSolvent

Procedure

To a solution of (3-carboxypropy)triphenylphosphonium bromide (25 g, 58.3 mmol) in DMSO (53 mL) was added t-BuOK (12.4 g, 110.7 mmol). The mixture was stirred at rt for 20 min. Then a solution of 3-Bromo-benzaldehyde (9.3 g, 50.3 mmol) in DMSO (15 mL) was added dropwise. The reaction mixture was stirred at rt for 4 h. The mixture was poured in water and extracted with DCM. The organic layer was dried over anhydrous sodium sulfate, filtered, and then concentrated under reduced pressure. The crude material was purified by silica gel chromatography using a solvent system of 5:1 petroleum ether/EtOAc to give 5-(3-Bromo-phenyl)-pent-4-enoic acid (4.8 g, 38%). 1H-NMR (400 MHz, CDCl3) δ ppm 7.45 (s, 1H), 7.2-7.25 (m, 1H), 7.1-7.15 (m, 2H), 6.4-6.45 (m, 1H), 6.23-6.3 (m, 1H), 2.4-2.6 (m, 4H).

Workup

  1. stirringThe reaction mixture was stirred at rt for 4 h
  2. extractionextracted with DCM
  3. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe crude material was purified by silica gel chromatography

Sources & evidence

ORD record
ord-77770eed8b8c4919849ffe213f8461d8
Source dataset
uspto-grants-2014_08
Patent number
US08796310B2

Reaction notes

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