Hydrochloric Acid → Methyl 2-(4-bromostyryl)benzoate

HRID 1085491Notes

Reaction equation

HRID 1085491 reaction equation
[Br-].[CH3:2][O:3][C:4]([C:6]1[CH:31]=[CH:30][CH:29]=[CH:28][C:7]=1[CH2:8][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)=[O:5].[H-].[Na+].[Br:34][C:35]1[CH:42]=[CH:41][C:38]([CH:39]=O)=[CH:37][CH:36]=1.Cl>O1CCCC1.CO.O>[Br:34][C:35]1[CH:42]=[CH:41][C:38]([CH:39]=[CH:8][C:7]2[CH:28]=[CH:29][CH:30]=[CH:31][C:6]=2[C:4]([O:3][CH3:2])=[O:5])=[CH:37][CH:36]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 707414-BromobenzaldehydeHCID 10743695{[2-(Methoxycarbonyl)phenyl]methyl}(triphenyl)phosphanium bromide

Product 1

HCID 53786368Methyl 2-(4-bromostyryl)benzoateYield 55.1%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

In 1.0 liter of tetrahydrofuran was suspended 60 g of (2-methoxycarbonylbenzyl)triphenylphosphonium bromide and, 3.2 g of sodium hydride was added to the suspension followed by stirring at room temperature for 3 hours. Then, 18 g of 4-bromobenzaldehyde was added and the mixture was stirred at room temperature for 2 hours. After completion of the reaction, 500 ml of water, 200 ml of methanol and 100 ml of 0.1 N hydrochloric acid aqueous solution were added thereto and the solvent was distilled off under reduced pressure. The residue was extracted with 500 ml of ethyl acetate. After washing in sequence with saturated sodium bicarbonate aqueous solution and then with saturated sodium chloride aqueous solution, the extract was dried over anhydrous magnesium sulfate and the solvent was distilled off under reduced pressure The resulting residue was recrystallized from methanol to give 17 g of methyl 2-(4-bromostyryl)benzoate as white needles.

Workup

  1. additionwas added to the suspension
  2. stirringthe mixture was stirred at room temperature for 2 hours
  3. additionwere added
  4. distillationthe solvent was distilled off under reduced pressure
  5. extractionThe residue was extracted with 500 ml of ethyl acetate
  6. washAfter washing in sequence with saturated sodium bicarbonate aqueous solution
  7. dry with materialwith saturated sodium chloride aqueous solution, the extract was dried over anhydrous magnesium sulfate
  8. distillationthe solvent was distilled off under reduced pressure The resulting residue
  9. customwas recrystallized from methanol

Sources & evidence

ORD record
ord-932b5c8fdeba423186d67898e8c7fee0
Source dataset
uspto-grants-1991_04
Patent number
US05010087

Reaction notes

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