Chloroform → 2-(1-Bromocyclohexyl)-8-cyanomethyl-4-oxo-4H-[1]-benzopyran

HRID 1200186Notes

Reaction equation

[C-:1]#[N:2].[Na+].C(Cl)(Cl)Cl.[Br:8][C:9]1([C:15]2[O:16][C:17]3[C:25]([CH2:26]Br)=[CH:24][CH:23]=[CH:22][C:18]=3[C:19](=[O:21])[CH:20]=2)[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]1>O.[Cl-].C([N+](C)(C)C)C1C=CC=CC=1>[Br:8][C:9]1([C:15]2[O:16][C:17]3[C:25]([CH2:26][C:1]#[N:2])=[CH:24][CH:23]=[CH:22][C:18]=3[C:19](=[O:21])[CH:20]=2)[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]1

Participants

Conditions

Temperature: 50 °C

Procedure

NaCN (3.88 g, 0.075 mole) was dissolved in water (11 ml) and to the solution was added benzyltrimethylammonium chloride (13.9 g, 0.075 mole). After stirring at 50° C. for 15 minutes, chloroform (120 ml) was added and further 2 -(1-bromocyclohexyl)-8-bromomethyl-4-oxo-4H-[1]-benzopyran (12 g, 0.03 mole) was added. The mixture was stirred for 4 hours. The chloroform layer was washed with water, dried (MgSO4) and then concentrated under reduced pressure to obtain crystals. The crude crystals were recrystallized from ethyl acetate to obtain the title compound (7.5 g) as prisms, m.p. 143°-144° C., yield 72.2%. IR and NMR spectra of this compound were identical with those of the compound obtained in Reference Example 20.

Workup

stirringThe mixture was stirred for 4 hours
washThe chloroform layer was washed with water
dry with materialdried (MgSO4)
concentrationconcentrated under reduced pressure
customto obtain crystals
customThe crude crystals were recrystallized from ethyl acetate

Sources & evidence

ORD record: ord-df6218633a364984a6efef2022b93e8d
Source dataset: uspto-grants-1990_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04904690

Reaction notes

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