Triethyl Phosphate → HCID 86670952, compound

HRID 515306Notes

Reaction equation

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

Participants

Reactant 2

HCID 6535Triethyl Phosphate2×

HCID 534033971-(Bromomethyl)-2,5-difluoro-4-nitrobenzene

Product 1

HCID 86670952HCID 86670952, compound

Conditions

Temperature: 140 °C

Procedure

1-(Bromomethyl)-2,5-difluoro-4-nitrobenzene (8.3 g, 32.9 mmol) and triethyl phosphate (12.03 mL) were heated in an oil bath for 2.5 hours at 140° C. Additional triethyl phosphate (5 mL) was added and the reaction was stirred at 140° C. for 1 hour. The reaction mixture was evaporated under reduced pressure and chromatographed on silica eluting with dichloromethane/methanol (1:0-1%) to give the title compound (11 g, 35.6 mmol). 1H NMR (CDCl3, 400 MHz): δ 7.82 (dd, 1H), 7.37 (ddd, 1H), 4.11 (m, 4H), 3.24 (d, 2H), 1.30 (m, 6H)

Workup

customThe reaction mixture was evaporated under reduced pressure
customchromatographed on silica eluting with dichloromethane/methanol (1:0-1%)

Sources & evidence

ORD record: ord-5215bd389ce14b568747bb0168d08f3d
Source dataset: uspto-grants-2015_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09108939B2

Reaction notes

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