Ethanol → Ethyl 4-(bromomethyl)benzoate

HRID 1168901Notes

Reaction equation

HRID 1168901 reaction equation
[CH:1]1(N=C=NC2CCCCC2)CCCC[CH2:2]1.[C:16]([C:19]1[CH:26]=[CH:25][C:22]([CH2:23][Br:24])=[CH:21][CH:20]=1)([OH:18])=[O:17].C(O)C>C(Cl)Cl.CN(C)C1C=CN=CC=1>[C:16]([C:19]1[CH:26]=[CH:25][C:22]([CH2:23][Br:24])=[CH:21][CH:20]=1)([O:18][CH2:1][CH3:2])=[O:17]

Participants

6

Reactant 3

HCID 702EthanolHCID 10868DicyclohexylcarbodiimideHCID 225994-(Bromomethyl)benzoic acid

Product 1

HCID 954261Ethyl 4-(bromomethyl)benzoate

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent3×

Procedure

To a stirred solution of 16.09 g (78 mmol) of 1,3-dicyclohexylcarbodiimide (Aldrich) in 100 ml methylene chloride was added a suspension of 15.4 g (71 mmol) of 4-carboxybenzylbromide in 100 ml methylene chloride and then 4.9 g (106.5 mmol) of absolute ethanol and 0.81 g (7.1 mmol) of 4-dimethylaminopyridine. A further 50 ml of methylene chloride was added to the reaction mixture and mixture heated at reflux for 2 hours. The mixture was allowed to cool to room temperature and the resultant white precipitate removed by filtration. The filtrate was washed with water, dried (MgSO4) and then concentrated in-vacuo to give the title compound as a colorless oil which crystallized on standing. PMR (CDCl3); δ 1.39 (3H, t, J=7.2 Hz), 4.38 (2H, q, J=7.2 Hz), 4.50 (2H, s), 7.45 (2H, d, J=7.7 Hz), 8.03 (2H, d, J=7.7 Hz).

Workup

  1. temperatureheated
  2. temperatureat reflux for 2 hours
  3. customthe resultant white precipitate removed by filtration
  4. washThe filtrate was washed with water
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated in-vacuo

Sources & evidence

ORD record
ord-351ad91ad6d449c4b9e51bee15d2d2c8
Source dataset
uspto-grants-2003_09
Patent number
US06627652B1

Reaction notes

Loading…