Triethylamine → Methanesulfonic acid 4-[1-(3-bromo-phenyl)-vinyl]-phenyl ester

HRID 1668730Notes

Reaction equation

[Br:1][C:2]1[CH:3]=[C:4]([C:8]([C:10]2[CH:15]=[CH:14][C:13]([OH:16])=[CH:12][CH:11]=2)=[CH2:9])[CH:5]=[CH:6][CH:7]=1.C(N(CC)CC)C.[CH3:24][S:25](Cl)(=[O:27])=[O:26].C(OCC)(=O)C.C1CCCCC1>ClCCl>[Br:1][C:2]1[CH:3]=[C:4]([C:8]([C:10]2[CH:11]=[CH:12][C:13]([O:16][S:25]([CH3:24])(=[O:27])=[O:26])=[CH:14][CH:15]=2)=[CH2:9])[CH:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of 4-[1-(3-bromo-phenyl)-vinyl]-phenol (1.5 g, 5.45 mmol, 1.0 eq) in dichloromethane (15 mL), triethylamine (2.26 mL, 16.35 mmol, 3.0 eq) was added and the reaction mixture cooled to 0° C. Then methanesulfonyl chloride (0.465 mL, 6.0 mmol, 1.1 eq) was added dropwise and the mixture was allowed to warm to room temperature and stirred 16 h. The reaction was examined by TLC (ethyl acetate/cyclohexane 20%) which showed complete conversion to the desired product. After night time water was added and organic and water phase were separated. Organic solution was dried over magnesium sulfate filtered and evaporated. The crude was purified by flash chromatography eluting with cyclohexane, then ethyl acetate/cyclohexane 20%. 1.6 g of clean product was obtained as colorless liquid (yield: 65%).

Workup

temperatureto warm to room temperature

Sources & evidence

ORD record: ord-1941588f36d04b59a8090498b8893c70
Source dataset: uspto-grants-2011_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07989449B2

Reaction notes

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