Triethyl phosphite → Methyl 4-[(diethoxyphosphoryl)methyl]-3-fluorobenzoate

HRID 230782Notes

Reaction equation

Br[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]([O:11][CH3:12])=[O:10])=[CH:5][C:4]=1[F:13].[P:14]([O:21]CC)([O:18][CH2:19][CH3:20])[O:15][CH2:16][CH3:17]>>[CH2:16]([O:15][P:14]([CH2:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]([O:11][CH3:12])=[O:10])=[CH:5][C:4]=1[F:13])([O:18][CH2:19][CH3:20])=[O:21])[CH3:17]

Participants

Reactant 2

HCID 31215Triethyl phosphite

HCID 18766370Methyl 4-(bromomethyl)-3-fluorobenzoate

Product 1

HCID 23498922Methyl 4-[(diethoxyphosphoryl)methyl]-3-fluorobenzoate

Conditions

Temperature: 145 °C

Procedure

A mixture of methyl 4-bromomethyl-3-fluorobenzenecarboxylate (240 mg) and triethyl phosphite (0.32 mL) was heated at 145° C. for 2 hours. The reaction solution was purified through silica gel column chromatography (ethyl acetate/methanol=9/1) to obtain the entitled compound (300 mg).

Workup

customThe reaction solution was purified through silica gel column chromatography (ethyl acetate/methanol=9/1)

Sources & evidence

ORD record: ord-74b227b3be194ed780e3d63d6ff7f6c1
Source dataset: uspto-grants-2009_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07566781B2

Reaction notes

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