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With phosphorus tribromide In diethyl ether at 0℃; for 0.5 h; Inert atmosphere
General procedure: Under inert atmosphere, phosphorus tribromide (1.2 equiv.) was added to a solution of benzyl alcohol derivative 24-25 (1 equiv.) in dry ether at 0 °C and then stirred for 30 min until the complete consumption of the benzyl alcohol (1H NMR control). After evaporation in vacuo of the ether, dichloromethane was added and the solution was washed with water multiple times. The organic phase was then dried over MgSO4 and concentrated giving the benzyl bromide 16-17 which was further used without additional purification in the N-alkylation reaction to provide compounds 5, 7 and 10.
Reference：
[1] Journal of Fluorine Chemistry, 1995, vol. 70, # 1, p. 39 - 44
[2] Bioorganic and Medicinal Chemistry, 2016, vol. 24, # 22, p. 6021 - 6030
2
[ 26412-87-3 ]
[ 405-09-4 ]
[ 331-64-6 ]
Yield
Reaction Conditions
Operation in experiment
88%
With potassium hydrogensulfate; triethylamine In dimethyl sulfoxide
4 2-fluoro-4-methoxybenzaldehyde Triethylamine (0.92 ml, 6.60 mmol) was added to a solution of 2-fluoro-4-methoxybenzylalcohol (346.9 mg, 2.22 mmol) in DMSO (8 ml). Pyridine sulfur trioxide (1.0501 g, 6.60 mmol) was added portionwise to the mixture checking raise of the temperature. The mixture was stirred for 0.5 hours. The mixture was added to 5percent KHSO4 aqueous solution, extracted three times with ethyl acetate and dried over MgSO4. The mixture was concentrated and purified by silica gel chromatography (hexane/ether=5/1) to give the title compound (301 mg; 88percent). 1H-NMR(CDCl3) 10.21 (s, 1H), 7.83 (t, 1H, J =8.3 Hz), 6.79 (ddd, 1H, J=8.3, 2.3, 0.7 Hz), 6.65 (dd, 1H, J=12.2, 2.3 Hz), 3.88 (s, 3H)
3 2-fluoro-4-methoxybenzylalcohol To a suspension of LiAlH4 (71.6 mg, 1.89 mmol) in THF (3 ml) was added dropwise a solution of <strong>[128272-26-4]methyl 2-fluoro-4-methoxybenzoate</strong> (273.3 mg, 1.48 mmol) in THF (3 ml). The mixture was stirred for 0.5 hours. To the mixture was added dropwise aqueous THF followed by water. The mixture was extracted three times with ethyl acetate and dried over MgSO4. The solvent was evaporated to give the crude title compound (240.4 mg; >99%). 1H-NMR(CDCl3) 7.29 (t, 1H, J=8.6 Hz), 6.69 (dd, 1H, J=8.6, 2.6 Hz), 6.63 (dd, 1H, J=11.7, 2.6 Hz), 4.68 (d, 2H, J=5.0 Hz), 3.80 (s, 3H), 1.65 (t, 1H, J=5.0 Hz)
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