Bromoacetonitrile → (4-Ethyl-7-methyl-benzo[b]thiophen-5-yloxy)-acetonitrile

HRID 38428Notes

Reaction equation

[CH2:1]([C:3]1[C:11]2[CH:10]=[CH:9][S:8][C:7]=2[C:6]([CH3:12])=[CH:5][C:4]=1[OH:13])[CH3:2].[H-].[Na+].Br[CH2:17][C:18]#[N:19]>CN(C=O)C>[CH2:1]([C:3]1[C:11]2[CH:10]=[CH:9][S:8][C:7]=2[C:6]([CH3:12])=[CH:5][C:4]=1[O:13][CH2:17][C:18]#[N:19])[CH3:2]

Participants

Conditions

Temperature: 0 °C

Procedure

4-Ethyl-7-methyl-benzo[b]thiophen-5-ol (438 mg, 2 mmol) was dissolved in 10 ml DMF, and the reaction mixture was cooled to zero degrees C. Sodium hydride (66 mg, 3 mmol) was added and the reaction mixture was stirred 30 minutes at zero C. Bromoacetonitrile (170 ul, 3 mmol) was added, and the reaction mixture was stirred 10 minutes at zero degrees C., then allowed to warm to room temperature. The reaction was quenched after 1 hour at room temperature with water, diluted with ethyl acetate, washed with water, brine, and dried over magnesium sulfate. Solvent was removed in vacuo, and the residue chromatographed (10% ethyl acetate in hexanes) to give 422 mg of (4-Ethyl-7-methyl-benzo[b]thiophen-5-yloxy)-acetonitrile as an oil, 80%.

Workup

stirringthe reaction mixture was stirred 10 minutes at zero degrees C
temperatureto warm to room temperature
customThe reaction was quenched after 1 hour at room temperature with water
additiondiluted with ethyl acetate
washwashed with water, brine
dry with materialdried over magnesium sulfate
customSolvent was removed in vacuo
customthe residue chromatographed (10% ethyl acetate in hexanes)

Sources & evidence

ORD record: ord-e586f13d43dd434c8baf6cd93473a7e4
Source dataset: uspto-grants-2013_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08524725B2

Reaction notes

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