Triethylamine → HCID 57825247, compound

HRID 1668728Notes

Reaction equation

[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:10]2[CH:15]=[CH:14][C:13]([OH:16])=[CH:12][CH:11]=2)=[CH2:9])=[CH:4][C:3]=1[Br:17].C(N(CC)CC)C.[CH3:25][S:26](Cl)(=[O:28])=[O:27].[C:30](OCC)(=O)C.C1CCCCC1>C(Cl)Cl>[Br:17][C:3]1[CH:4]=[C:5]([C:8]([C:10]2[CH:15]=[CH:14][C:13]([O:16][S:26]([CH3:25])(=[O:28])=[O:27])=[C:12]([CH3:30])[CH:11]=2)=[CH2:9])[CH:6]=[CH:7][C:2]=1[F:1]

Participants

Conditions

Temperature: 0 °C

Procedure

4-[1-(4-Fluoro-3-bromo-phenyl)-vinyl]-phenol was produced from {4-[1-(3-bromo-4-fluoro-phenyl)-vinyl]-phenoxy}-tert-butyl-dimethyl-silane according to Building Block X & AA. To a solution of 4-[1-(4-fluoro-3-bromo-phenyl)-vinyl]-phenol (1.5 g, 4.88 mmol, 1.0 eq) in DCM (15 mL), triethylamine (2.0 mL, 14.65 mmol, 3.0 eq) was added and the reaction mixture cooled to 0° C. Then methanesulfonyl chloride (0.416 mL, 5.37 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%. 1.4 g of clean product was obtained as colorless liquid (yield: 75%)

Workup

temperatureto warm to room temperature

Sources & evidence

ORD record: ord-136db931c8744c018b79b8adf1f06c7e
Source dataset: uspto-grants-2011_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07989449B2

Reaction notes

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