1-Bromo-2-Chloroethane → 1-(2,3-dihydro-1H-inden-6-yl)cyclopropanecarbonitrile

HRID 869856Notes

Reaction equation

[CH2:1]1[C:9]2[C:4](=[CH:5][C:6]([CH2:10][C:11]#[N:12])=[CH:7][CH:8]=2)[CH2:3][CH2:2]1.[OH-].[Na+].Br[CH2:16][CH2:17]Cl>C1(C)C=CC=CC=1.[N+](CCCC)(CCCC)(CCCC)CCCC.[Br-].O>[CH2:3]1[C:4]2[C:9](=[CH:8][CH:7]=[C:6]([C:10]3([C:11]#[N:12])[CH2:17][CH2:16]3)[CH:5]=2)[CH2:1][CH2:2]1

Participants

Conditions

Temperature: 60 °C

Procedure

To a stirred solution of 2-(2,3-dihydro-1H-inden-5-yl)acetonitrile (50.0 g, 0.32 mol) in toluene (150 mL) was added sodium hydroxide (300 mL, 50 percent in water W/W), 1-bromo-2-chloroethane (92.6 ml, 1.12 mol) and (n-Bu)4NBr (5 g, 15.51 mmol). The mixture was heated at 60° C. overnight. After cooling to room temperature, the reaction mixture was diluted with water (400 mL) and extracted with EtOAc (3×200 mL). The combined organic extracts were washed with brine, dried over Na2SO4, filtered and concentrated under vacuum and purified by column chromatography (petroleum ether:ethyl acetate=10:1) to yield 1-(2,3-dihydro-1H-inden-6-yl)cyclopropanecarbonitrile (9.3 g, 16%). 1H NMR (CDCl3,300 MHz) δ 1.35-1.38 (m, 2H), 1.66-1.69 (m, 2H), 2.05-2.13 (m, 2H), 2.87-294 (m, 4H), 7.07-7.22 (m, 3H).

Workup

temperatureAfter cooling to room temperature
extractionextracted with EtOAc (3×200 mL)
washThe combined organic extracts were washed with brine
dry with materialdried over Na2SO4
filtrationfiltered
concentrationconcentrated under vacuum
custompurified by column chromatography (petroleum ether:ethyl acetate=10:1)

Sources & evidence

ORD record: ord-2d39ce5dc6184858a80d254cd88097a4
Source dataset: uspto-grants-2015_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08969386B2

Reaction notes

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