o-Fluorobenzaldehyde → HCID 86673445, compound

HRID 2362423Notes

Reaction equation

[Br:1][C:2]1[N:7]=[C:6]([CH2:8]P(=O)(OCC)OCC)[CH:5]=[CH:4][CH:3]=1.[F:17][C:18]1[CH:25]=[CH:24][CH:23]=[CH:22][C:19]=1[CH:20]=O.CC(C)([O-])C.[K+]>O1CCCC1>[Br:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6](/[CH:8]=[CH:20]/[C:19]2[CH:22]=[CH:23][CH:24]=[CH:25][C:18]=2[F:17])[N:7]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of diethyl (6-bromopyridin-2-yl)methylphosphonate (320 mg, 1.039 mmol) in tetrahydrofuran (9.4 mL) was added 2-fluorobenzaldehyde (129 mg, 1.04 mmol). The resulting solution was cooled to 0° C., and treated with potassium tert-butoxide (1M in tetrahydrofuran, 1.1 mL, 1.1 mmol). After 15 min at 0° C., the reaction was quenched by addition of saturated ammonium chloride and concentrated. The resulting residue was dissolved in ether, washed with water, then brine, dried over magnesium sulfate, and concentrated to give an oil which solidified upon standing. The solid was triturated with hexane to afford 215 mg (78%). 1H NMR (CDCl3) δ: 7.78 (d, J=16.2 Hz, 1H), 7.64 (td, J=7.6, 1.5 Hz, 1H), 7.50-7.58 (m, 1H), 7.37 (t, J=7.8 Hz, 2H), 7.29-7.34 (m, 1H), 7.15-7.26 (m, 2H), 7.12 (dd, J=10.5, 8.7 Hz, 1H). 13C NMR (CDCl3) δ: 161.1, 157.0, 142.3, 138.9, 130.1, 129.0, 128.4, 127.2, 126.5, 124.4, 124.2, 120.8, 116.1 19F NMR (CDCl3) δ: −116.28 (br. s., 1F). Mass spec.: 278.0 (MH)+.

Workup

customthe reaction was quenched by addition of saturated ammonium chloride
concentrationconcentrated
dissolutionThe resulting residue was dissolved in ether
washwashed with water
dry with materialbrine, dried over magnesium sulfate
concentrationconcentrated
customto give an oil which
customThe solid was triturated with hexane
customto afford 215 mg (78%)

Sources & evidence

ORD record: ord-d70daf73786449b2a2d18ebf549acffb
Source dataset: uspto-grants-2014_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08691821B2

Reaction notes

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