Triethylamine → Benzene, 2-fluoro-4-methoxy-1-(1-methylethenyl)-

HRID 604595Notes

Reaction equation

[F:1][C:2]1[CH:7]=[C:6]([O:8][CH3:9])[CH:5]=[CH:4][C:3]=1[C:10](O)([CH3:12])[CH3:11].CS(Cl)(=O)=O.C(N(CC)CC)C>C(Cl)Cl>[F:1][C:2]1[CH:7]=[C:6]([O:8][CH3:9])[CH:5]=[CH:4][C:3]=1[C:10]([CH3:12])=[CH2:11]

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of 2-(2-fluoro-4-methoxyphenyl)propan-2-ol (3.89 g, 21.14 mmol) in CH2Cl2 (50 mL) at 0° C., methylsulfonyl chloride (1.95 mL, 25.4 mmol) and triethylamine (6.52 mL, 46.5 mmol) were added. The solution was stirred at 0° C. and then room temperature for 2 h. The solution was diluted with CH2Cl2 (100 mL), washed with water, and dried over Na2SO4. The title compound was obtained as an oil after flash chromatography using EtOAc:hexane=1:9 as the eluant. 1H NMR (CDCl3, 500 MHz) δ 7.25 (t, J=9.0 Hz, 1H), 6.68 (dd, J=8.5, 2.5 Hz, 1H), 6.63 (dd, J=13, 2.5 Hz, 1H), 5.20 (d, J=17.0 Hz, 2H), 3.82 (s, 3H), 2.18 (s, 3H).

Workup

washwashed with water
dry with materialdried over Na2SO4

Sources & evidence

ORD record: ord-013b6630ece146149984f30dd4d4a654
Source dataset: uspto-grants-2011_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07910592B2

Reaction notes

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