Carbon tetrabromide → HCID 178511232, compound

HRID 370703Notes

Reaction equation

[Br:1][C:2]([Br:5])(Br)Br.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:25]([C@H:27]1[CH2:32][CH2:31][C@H:30]([CH:33]=O)[CH2:29][CH2:28]1)#[N:26]>C(Cl)Cl>[Br:1][C:2]([Br:5])=[CH:33][C@H:30]1[CH2:31][CH2:32][C@H:27]([C:25]#[N:26])[CH2:28][CH2:29]1

Participants

Conditions

Temperature: -10 °C

Procedure

A solution of 24.0 g of tetrabromomethane in 100 ml of methylene chloride was placed at -15° C. in a sulphonation flask under argon gasification and treated within 10 minutes with a solution of 38.0 of triphenylphosphine in 50 ml of methylene chloride. The clear orange solution was stirred at -10° C. for a further 10 minutes and subsequently a solution of 5.0 g of trans-4-cyanocyclohexanecarboxaldehyde in 20 ml of methylene chloride was added dropwise thereto at -5° C. within 10 minutes. The mixture was stirred at 0° C. for a further 30 minutes, then poured into 1 l of 10% ethyl acetate/petroleum ether and freed from precipitated triphenylphosphine oxide by filtration. The concentrated filtrate was again digested with 500 ml of 10% ethyl acetate/petroleum ether, filtered and concentrated. Low-pressure chromatography (0.5 bar) of the residue (14 g) on silica gel with 10% ethyl acetate/petroleum ether gave 11.0 g of trans-4-(2,2-dibromovinyl)cyclohexanecarbonitrile which was still contaminated with triphenylphosphine. A second low-pressure chromatography of this material on silica gel with 3% ethyl acetate/petroleum ether gave 9.04 g (85%) of pure trans-4-(2,2-dibromovinyl)cyclohexanecarbonitrile, m.p. 77.5°-78.5° C.

Workup

waitat -5° C. within 10 minutes
stirringThe mixture was stirred at 0° C. for a further 30 minutes
customfrom precipitated triphenylphosphine oxide
filtrationby filtration
filtrationfiltered
concentrationconcentrated

Sources & evidence

ORD record: ord-163e8e128daa475baab6f301d7485845
Source dataset: uspto-grants-1985_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04528114

Reaction notes

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