Triethyl phosphite → Phosphonic acid, [(4-fluoro-3-phenoxyphenyl)methyl]-, diethyl ester

HRID 479889Notes

Reaction equation

HRID 479889 reaction equation
[F:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6]Br)=[CH:4][C:3]=1[O:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.[P:17]([O:24]CC)([O:21][CH2:22][CH3:23])[O:18][CH2:19][CH3:20]>>[F:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][P:17](=[O:24])([O:21][CH2:22][CH3:23])[O:18][CH2:19][CH3:20])=[CH:4][C:3]=1[O:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

3

Reactant 2

HCID 31215Triethyl phosphiteHCID 129227144-(Bromomethyl)-1-fluoro-2-phenoxybenzene

Product 1

HCID 11279166Phosphonic acid, [(4-fluoro-3-phenoxyphenyl)methyl]-, diethyl esterYield 95%

Conditions

Temperature
90 °C

Procedure

A mixture of 4-fluoro-3-phenoxybenzyl bromide (28.1 g, 100 mmol) and triethyl phosphite (18.27 g, 110 mmol) is heated at 90° C. for 30 minutes while allowing some low boiling materials to distill off. The resultant mixture is heated at 140° C. for 3.5 hours and distilled at 120° C./2 mmHg to give the title product as a syrup (32.1 g, 95% yield) which is identified by 1H and 19F NMR spectral analyses.

Workup

  1. distillationto distill off
  2. temperatureThe resultant mixture is heated at 140° C. for 3.5 hours
  3. distillationdistilled at 120° C./2 mmHg

Sources & evidence

ORD record
ord-ba7c63ed7a65428db5fdc7f18aa76aac
Source dataset
uspto-grants-2003_11
Patent number
US06646166B1

Reaction notes

Loading…