Boron tribromide → 5-{2-[5-Chloro-2-(hydroxy)-phenyl]cyclopent-1-enyl}-nicotinic Acid Ethyl Ester

HRID 1767194Notes

Reaction equation

[CH2:1]([O:3][C:4](=[O:25])[C:5]1[CH:10]=[C:9]([C:11]2[CH2:15][CH2:14][CH2:13][C:12]=2[C:16]2[CH:21]=[C:20]([Cl:22])[CH:19]=[CH:18][C:17]=2[O:23]C)[CH:8]=[N:7][CH:6]=1)[CH3:2].B(Br)(Br)Br>ClCCl>[CH2:1]([O:3][C:4](=[O:25])[C:5]1[CH:10]=[C:9]([C:11]2[CH2:15][CH2:14][CH2:13][C:12]=2[C:16]2[CH:21]=[C:20]([Cl:22])[CH:19]=[CH:18][C:17]=2[OH:23])[CH:8]=[N:7][CH:6]=1)[CH3:2]

Participants

Conditions

Temperature: -75 °C

Procedure

5-{2-[5-Chloro-2-(methoxy)-phenyl]-cyclopent-1-enyl}-nicotinic acid ethyl ester (1.500 g, 4.20 mmol) in dry dichloromethane (20 mL) was cooled to −75° C. Boron tribromide, 1M solution in DCM, (40 mL, 40.0 mmol) was added and the reaction mixture stirred at −75° C. for a further hour. The temperature of the reaction was then allowed to rise to −15° C. and kept at −15° C. for a further 2 hours, and was then quenched in ice/water (50 g/50 mL). More dichloromethane (60 mL) was added and the resulting mixture was stirred vigorously for ˜2 hrs. The layers were separated and the organic layer was washed with saturated sodium bicarbonate, dried (magnesium sulphate), filtered and reduced to an oil. The oil was then purified by chromatography to give the title compound (0.800 g, 60%).

Workup

customto rise to −15° C.
customwas then quenched in ice/water (50 g/50 mL)
additionMore dichloromethane (60 mL) was added
stirringthe resulting mixture was stirred vigorously for ˜2 hrs
customThe layers were separated
washthe organic layer was washed with saturated sodium bicarbonate
dry with materialdried (magnesium sulphate)
filtrationfiltered
customThe oil was then purified by chromatography

Sources & evidence

ORD record: ord-810795db9cc04b25a78ef4dbe0f8f26e
Source dataset: uspto-grants-2007_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07232821B2

Reaction notes

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