Toluene → Ethyl 4-(dimethoxyphosphorylmethyl)-3-trifluoromethylbenzoate

HRID 13757

Reaction equation

HRID 13757 reaction equation
Br[CH2:2][C:3]1[CH:13]=[CH:12][C:6]([C:7]([O:9][CH2:10][CH3:11])=[O:8])=[CH:5][C:4]=1[C:14]([F:17])([F:16])[F:15].C1(C)C=CC=CC=1.[P:25]([O:30]C)([O:28][CH3:29])[O:26][CH3:27]>>[CH3:27][O:26][P:25]([CH2:2][C:3]1[CH:13]=[CH:12][C:6]([C:7]([O:9][CH2:10][CH3:11])=[O:8])=[CH:5][C:4]=1[C:14]([F:17])([F:16])[F:15])([O:28][CH3:29])=[O:30]

Participants

4

Reactant 3

HCID 1140TolueneHCID 8472Trimethyl phosphiteHCID 23073576Ethyl 4-(bromomethyl)-3-(trifluoromethyl)benzoate

Product 1

HCID 23145856Ethyl 4-(dimethoxyphosphorylmethyl)-3-trifluoromethylbenzoate

Procedure

6.20 g of ethyl 4-(bromomethyl)-3-trifluoromethylbenzoate (Reference Example 2 (step 2)) was dissolved in 12 ml of trimethyl phosphite and the mixture was heated at reflux for 4 hours under an argon atmosphere. After the completion of the reaction, the operation of adding of toluene to the residue, followed by azeotropic removal of trimethyl phosphite was repeated three times. The residue was purified by silica gel column chromatography to obtain 4.96 g of the objective compound as a yellow oily product.

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux for 4 hours under an argon atmosphere
  3. customAfter the completion of the reaction
  4. customfollowed by azeotropic removal of trimethyl phosphite
  5. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-e8b8ff3cc5994df4a322785abc0d4ca2
Source dataset
uspto-grants-2010_06
Patent number
US07728131B2

Linked notes

Loading…