N-Fluorobenzenesulfonimide → 2-Methoxy-6-(4-methoxyphenyl)-1-fluoronaphthalene

HRID 1830631Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:12]=[CH:11][C:10]2[C:5](=[CH:6][CH:7]=[C:8]([C:13]3[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=3)[CH:9]=2)[C:4]=1Br.C([Li])CCC.C1C=CC(S(N(S(C2C=CC=CC=2)(=O)=O)[F:37])(=O)=O)=CC=1>C1COCC1.O>[CH3:1][O:2][C:3]1[CH:12]=[CH:11][C:10]2[C:5](=[CH:6][CH:7]=[C:8]([C:13]3[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=3)[CH:9]=2)[C:4]=1[F:37]

Participants

Conditions

Temperature: -78 °C

Procedure

To a solution of 2-methoxy-6-(4-methoxyphenyl)-1-bromonaphthalene (1.28 g, 3.72 mmol) in THF (25 mL) at −78° C. was slowly added n-butyl lithium (1.9 mL of 2.5 N in hexanes). The resulting solution was stirred at −78° C. for thirty minutes and a solution of N-fluorobenzenesulfonimide (1.40 g, 4.5 mmol) in THF (10 mL) was added. After 2 additional hr at −78° C., the reaction was warmed to room temperature, poured in water, and extracted with ethyl acetate (2×250 mL). The combined organic layers were washed with water, dried over sodium sulfate, filtered, evaporation of the solvent, and purification by silica chromatography (5% THF-hexanes) yielded 0.66 g (63%) of a white solid: Mfp 150–155° C.; 1H NMR (CDCl3): δ 3.88 (3H, s), 4.04 (3H, s), 7.02 (2H, d, J=8.69 Hz), 7.28–7.34 (1H, m), 7.62–7.67 (3H, m), 7.74 (1H, dd, J=1.60 Hz, J=8.79 Hz), 7.93 (1H, s), 8.09 (1H, d, J=8.77 Hz).

Workup

customat −78° C.
temperatureAfter 2 additional hr at −78° C., the reaction was warmed to room temperature
extractionextracted with ethyl acetate (2×250 mL)
washThe combined organic layers were washed with water
dry with materialdried over sodium sulfate
filtrationfiltered
customevaporation of the solvent, and purification by silica chromatography (5% THF-hexanes)

Sources & evidence

ORD record: ord-13a39872b1ab46e2b25172825416b7bc
Source dataset: uspto-grants-2006_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07067524B2

Reaction notes

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