Triethyl phosphite → Diethyl (4-Bromobenzyl)phosphonate

Reaction equation

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

Participants

Reactant 2

HCID 31215Triethyl phosphite

HCID 685274-Bromobenzyl bromide

Product 1

HCID 11077666Diethyl (4-Bromobenzyl)phosphonateYield 89.5%

Conditions

Temperature: 130 °C

Procedure

203.6 g (815 mmol) of 4-bromobenzyl bromide and 215 ml (1.2 mol) of triethyl phosphite are mixed and heated at 130° C. for 1 h with gas discharge. The product is then subjected to fractional distillation (2×10−2 mbar, 120° C.), giving 224 g (89%) of the product as a colourless liquid.

Workup

distillationThe product is then subjected to fractional distillation (2×10−2 mbar, 120° C.)

Sources & evidence

ORD record: ord-cb0e7c1eedf84d188c7c7051d1f26aee
Source dataset: uspto-grants-2010_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07799875B2

Reaction notes

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