Methyl iodide → Methyl 3-(2-bromophenyl)propanoate

HRID 986552Notes

Reaction equation

HRID 986552 reaction equation
CI.[Br:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[CH2:10][CH2:11][C:12]([OH:14])=[O:13].[C:15](=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[Br:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[CH2:10][CH2:11][C:12]([O:14][CH3:15])=[O:13]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 3160103-(2-Bromophenyl)propionic acid

Product 1

HCID 15712815Methyl 3-(2-bromophenyl)propanoateYield 95%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Methyl iodide (51 g, 22.4 ml, 0.24 mole) was added to a stirred mixture of 3-(2-bromophenyl)propanoic acid (36.7 g, 0.16 mole, prepared as described by F. G. Holliman and F. G. Mann J Chem. Soc. 9, 1960) and anhydrous potassium carbonate (33 g, 0.24 mole) in dry N,N-dimethylformamide (250 ml) and the mixture was stirred at ambient temperature overnight. After removal of the solvent in vacuo the residue was partitioned between ether and water and the ethereal phase washed with aqueous sodium thiosulphate and then brine and dried (MgSO4). Evaporation gave a pale yellow oil which distilled at 116°-118° C. (0.2 mm) to give 36.91 g (95%) of the title ester as a colourless oil, νmax 2950, 1740, 1570, 1470, 1440 cm-1, δ(CDCl3), 2.63 (2H, m, ArCH2), 3.07 (2H, m, CH2CO2), 3.70 (3H, s, CH3), 7.12 (3H, m, arom), 7.50 (1H, d, arom).

Workup

  1. customAfter removal of the solvent in vacuo the residue
  2. customwas partitioned between ether and water
  3. washthe ethereal phase washed with aqueous sodium thiosulphate
  4. dry with materialbrine and dried (MgSO4)
  5. customEvaporation
  6. customgave a pale yellow oil which
  7. distillationdistilled at 116°-118° C. (0.2 mm)

Sources & evidence

ORD record
ord-13f09688d9534085b948692dcdb8d7e6
Source dataset
uspto-grants-1987_12
Patent number
US04713486

Reaction notes

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