Acetonitrile → HCID 11325431, compound

HRID 902406Notes

Reaction equation

C([Li])CCC.[C:6](#[N:8])[CH3:7].[CH2:9]([O:16][C:17]1[C:18]([O:26][CH3:27])=[CH:19][C:20]([CH2:24]Br)=[C:21]([Br:23])[CH:22]=1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1>CCCCCC.O1CCCC1>[CH2:9]([O:16][C:17]1[C:18]([O:26][CH3:27])=[CH:19][C:20]([CH2:24][CH2:7][C:6]#[N:8])=[C:21]([Br:23])[CH:22]=1)[C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1

Participants

Conditions

Temperature: -78 °C

Procedure

To a solution of n-butyllithium (1.8 mL of a 2.5 M solution in hexane, 4.5 mmol) in 5 mL of tetrahydrofuran is added a solution of acetonitrile (1.0 mL, 19.1 mmol) in 5 mL of tetrahydrofuran. The reaction mixture is stirred at −78° C. for 15 min. A solution of 5-(benzyloxy)-1-bromo-2-(bromomethyl)-4-methoxybenzene (0.7 g, 1.8 mmol) in 3 mL of tetrahydrofuran is added and stirring is continued for 1 hour at −78° C. The reaction is quenched by the addition of 15 mL of water and the mixture is allowed to warm to room temperature. The mixture is extracted with ethyl acetate and the organic layers combined, then dried with sodium sulfate. After reducing in vacuo, the crude product is purified by flash chromatography using a gradient of 95:5 to 4:1 hexanes/ethyl acetate as an eluent. The clean fractions are combined, reduced in vacuo and dried to yield 0.343 g of 3-(4-benzyloxy-2-bromo-5-methoxyphenyl)-propionitrile as a white solid, mp 52-53° C.

Workup

stirringstirring
waitis continued for 1 hour at −78° C
customThe reaction is quenched by the addition of 15 mL of water
temperatureto warm to room temperature
extractionThe mixture is extracted with ethyl acetate
dry with materialdried with sodium sulfate
customthe crude product is purified by flash chromatography
customdried

Sources & evidence

ORD record: ord-0fee426e4fa74830b250e16f15a8c053
Source dataset: uspto-grants-2008_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07365197B2

Reaction notes

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