Carbon tetrabromide → 5-(Bromomethyl)furan-2-carbonitrile

HRID 1952851Notes

Reaction equation

C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O[CH2:21][C:22]1[O:26][C:25]([C:27]#[N:28])=[CH:24][CH:23]=1.[Br:29]C(Br)(Br)Br>O1CCCC1>[Br:29][CH2:21][C:22]1[O:26][C:25]([C:27]#[N:28])=[CH:24][CH:23]=1

Participants

Conditions

Temperature: -10 °C

Procedure

38 g (145 mmol) triphenylphosphine were added to a solution of 15 g (121 mol [sic]) of 5-hydroxymethyl-2-cyanofuran in 250 ml of tetrahydrofuran. The mixture was cooled to -10° C., and a solution of 48 g (145 mmol) of tetrabromomethane in 100 ml of tetrahydrofuran was added. The mixture was allowed to warm to room temperature and was stirred at this temperature for 3 hours. The mixture was concentrated in a rotary evaporator under water pump vacuum and the residue was purified by column chromatography (mobile phase petroleum ether:dichloromethane 1:1, Rf =0.5). 11.5 g of the title compound were obtained. 1H-NMR (250 MHz, d6 -DMSO): δ=4.8 (m, 2H), 6.7 (d, 1H), 7.7 (d, 1H).

Workup

temperatureto warm to room temperature
concentrationThe mixture was concentrated in a rotary evaporator under water pump vacuum
customthe residue was purified by column chromatography (mobile phase petroleum ether:dichloromethane 1:1, Rf =0.5)

Sources & evidence

ORD record: ord-859db9be3a114095ab61aa2bca1dea29
Source dataset: uspto-grants-2000_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06114358

Reaction notes

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