2-(4-Bromobenzyl)malonic acid → 3-(4-Bromophenyl)propionic acid

HRID 931511Notes

Reaction equation

HRID 931511 reaction equation
[Br:1][C:2]1[CH:15]=[CH:14][C:5]([CH2:6][CH:7](C(O)=O)[C:8]([OH:10])=[O:9])=[CH:4][CH:3]=1>CS(C)=O>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][CH2:7][C:8]([OH:10])=[O:9])=[CH:14][CH:15]=1

Participants

3

Reactant 1

HCID 133302152-(4-Bromobenzyl)malonic acid

Product 1

HCID 27356093-(4-Bromophenyl)propionic acidYield 98%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A solution of 2-(4-bromobenzyl)malonic acid (18 g, 66.18 mmol, 1.00 equiv) in dimethylsulfoxide (50 mL) was stirred at 160° C. for 2 h. The reaction mixture was cooled to room temperature and the product was precipitated by the addition of 200 mL ice and water. The solid was collected by filtration, washed with 1×50 mL of water and dried in a vacuum oven to give 14.8 g (98%) of 3-(4-bromophenyl)propanoic acid as a white solid. LC-MS: (ES, m/z): 229 [M+H]+. 1HNMR (400 MHz, DMSO-d6, ppm): δ 7.45 (d, J=8.0 Hz, 2H), 7.21 (d, J=8.0 Hz, 2H), 2.82-2.77 (m, 2H), 2.55-2.51 (m, 2H).

Workup

  1. customthe product was precipitated by the addition of 200 mL ice and water
  2. filtrationThe solid was collected by filtration
  3. washwashed with 1×50 mL of water
  4. customdried in a vacuum oven

Sources & evidence

ORD record
ord-45abe453f59540788b1afb94807d32ff
Source dataset
uspto-grants-2016_03
Patent number
US09296732B2

Reaction notes

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