p-Toluenesulphonyl cyanide → HCID 59288356, compound

HRID 2420640Notes

Reaction equation

Br[C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][CH:7]([C:12]3[CH:21]=[C:20]4[C:15]([CH2:16][CH:17]([CH2:22][CH2:23][CH3:24])[CH2:18][O:19]4)=[CH:14][C:13]=3[F:25])[CH2:8][O:9]2)=[CH:4][C:3]=1[F:26].C([Li])CCC.C1(C)C=CC(S([C:41]#[N:42])(=O)=O)=CC=1>C1COCC1.CCCCCC.CCOCC>[F:26][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:2]=1[C:41]#[N:42])[O:9][CH2:8][CH:7]([C:12]1[CH:21]=[C:20]3[C:15]([CH2:16][CH:17]([CH2:22][CH2:23][CH3:24])[CH2:18][O:19]3)=[CH:14][C:13]=1[F:25])[CH2:6]2

Participants

Conditions

Temperature: -70 °C

Procedure

1.4 g (3.31 mmol) of 7-bromo-6,6′-difluoro-3′-propyl-3,4,3′,4′-tetrahydro-2H,2′H-[3,7′]bichromenyl are dissolved in 20 ml of THF, and 3 ml (4.8 mmol) of a 15 percent solution of n-butyl-lithium in hexane are added at −50° C. The batch is left to stir for 2 h at −70° C., and a solution of 0.9 g (5.00 mmol) of p-toluenesulfonyl cyanide in 10 ml of THF is subsequently added at such a rate that the temperature does not exceed −65° C. After 30 min, the batch is allowed to thaw, diluted with ether and washed with dil. hydrochloric acid. The org. phase is dried over sodium sulfate and evaporated, and the crude product is chromatographed on silica gel with heptane/toluene (2:3), giving 6,6′-difluoro-3′-propyl-3,4,3′,4′-tetrahydro-2H,2′H-[3,7]bichromenyl-7-carbonitrile as colourless crystals of m.p. 122° C.

Workup

waitThe batch is left
customdoes not exceed −65° C
waitAfter 30 min
washwashed with dil. hydrochloric acid
dry with materialphase is dried over sodium sulfate
customevaporated
customthe crude product is chromatographed on silica gel with heptane/toluene (2:3)

Sources & evidence

ORD record: ord-b0614d35ae63413685025c7769047b91
Source dataset: uspto-grants-2011_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07955664B2

Reaction notes

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