2-Fluoroethyl bromide → 1-(2-Fluoroethyl)-4-[3-(methyloxy)-4-nitrophenyl]pyridinium bromide

HRID 419554Notes

Reaction equation

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

Participants

Conditions

Temperature: 110 °C

Procedure

To 4-[3-(methyloxy)-4-nitrophenyl]pyridine (Example 137, step A) (2.3 g, 10 mmol) in pinacolone (25 mL) is added 1-bromo-2-fluoroethane (2.5 g, 20 mmol). The mixture was stirred at 110° C. in a sealed tube overnight. The solution was cooled to rt and the solid collected by vacuum filtration washing with acetone. The title compound of step A (2.0 g, 5.6 mmol, 56%) was obtained as a beige solid. 1H NMR (400 MHz, DMSO-d6) δ9.21 (d, J=7.0 Hz, 2H), 8.68 (d, J=7.3 Hz, 2H), 8.12 (d, J=8.4 Hz, 1H), 7.92 (d, J=1.8 Hz, 1H), 7.77 (dd, J=8.4, 1.8 Hz, 1H), 5.05 (s, 2H), 5.00-4.90 (m, 2H), 4.07 (s, 3H). MS (ESI) m/z=277 [M].

Workup

temperatureThe solution was cooled to rt
filtrationthe solid collected by vacuum filtration
washwashing with acetone

Sources & evidence

ORD record: ord-e7db74bdaa1042d298c43c3b333589cb
Source dataset: uspto-grants-2012_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08093239B2

Reaction notes

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