Methyl iodide → 2-Propenoic acid, 3-(4-bromophenyl)-, methyl ester

HRID 986542Notes

Reaction equation

HRID 986542 reaction equation
[C:1](=O)([O-])[O-].[K+].[K+].[Br:7][C:8]1[CH:18]=[CH:17][C:11]([CH:12]=[CH:13][C:14]([OH:16])=[O:15])=[CH:10][CH:9]=1.CI>CN(C)C=O>[Br:7][C:8]1[CH:9]=[CH:10][C:11]([CH:12]=[CH:13][C:14]([O:16][CH3:1])=[O:15])=[CH:17][CH:18]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 99777p-Bromocinnamic acid

Product 1

HCID 8167732-Propenoic acid, 3-(4-bromophenyl)-, methyl esterYield 94,283.602%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Anhydrous potassium carbonate (20.7 g, 0.15 mmole) was added to a solution of 4-bromocinnamic acid (22.7 g, 0.1 mmole) in dry N,N-dimethylformamide (150 ml) and the mixture was stirred for 30 minutes. Methyl iodide (21.3 g, 9.4 ml, 0.15 mmole) was then added and the total mixture stirred for a further 24 hours at room temperature before the solvent was evaporated in vacuo. Water was added to the residue and the product extracted into ether. The ethereal extracts were washed with saturated aqueous sodium bicarbonate solution, the brine and dried (MgSO4). Evaporation afforded 22.73 g (94%) of the ester as a white solid of mp (methanol) 82°-86° C. (lit mp 80° C., Dictionary of Organic Compounds), υmax (mull), 1718, 1640, 1595, 1495 cm-1. δ(CDCl3) 3.80 (3H, s, ester CH3), 6.37 (1H, d, J 13 Hz, =CHCO2), 7.42 (4H, m, arom), 7.62 (1H, d, J 13 Hz, ArCH=).

Workup

  1. stirringthe total mixture stirred for a further 24 hours at room temperature before the solvent
  2. customwas evaporated in vacuo
  3. additionWater was added to the residue
  4. extractionthe product extracted into ether
  5. washThe ethereal extracts were washed with saturated aqueous sodium bicarbonate solution
  6. dry with materialthe brine and dried (MgSO4)
  7. customEvaporation

Sources & evidence

ORD record
ord-5a2c02007c314316acc0252547aea7f8
Source dataset
uspto-grants-1987_12
Patent number
US04713486

Reaction notes

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