Triethyl phosphite → Methyl 4-(diethoxyphosphorylmethyl)benzoate

HRID 923443Notes

Reaction equation

HRID 923443 reaction equation
Br[CH2:2][C:3]1[CH:12]=[CH:11][C:6]([C:7]([O:9][CH3:10])=[O:8])=[CH:5][CH:4]=1.[P:13]([O:20]CC)([O:17][CH2:18][CH3:19])[O:14][CH2:15][CH3:16]>>[CH2:15]([O:14][P:13]([CH2:2][C:3]1[CH:12]=[CH:11][C:6]([C:7]([O:9][CH3:10])=[O:8])=[CH:5][CH:4]=1)([O:17][CH2:18][CH3:19])=[O:20])[CH3:16]

Participants

3

Reactant 2

HCID 31215Triethyl phosphiteHCID 256687Methyl 4-(bromomethyl)benzoate

Product 1

HCID 10946061Methyl 4-(diethoxyphosphorylmethyl)benzoate

Procedure

A solution of methyl 4-(bromomethyl)benzoate (12.5 g, 54.6 mmol) in triethyl phosphite (20 mL, 114 mmol) was heated at 150° C. for 2 hours. After cooling, the solution was concentrated under vacuum. Purification by chromatography (silica gel, 0-2% methanol in dichloromethane) afforded the title compound. MS (ESI) m/z 287 (M+H)+.

Workup

  1. temperatureAfter cooling
  2. concentrationthe solution was concentrated under vacuum
  3. customPurification by chromatography (silica gel, 0-2% methanol in dichloromethane)

Sources & evidence

ORD record
ord-c73feee6c93d4203b8e2798f0c973d87
Source dataset
uspto-grants-2016_03
Patent number
US09278922B2

Reaction notes

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