Water → 2-(2-Bromo-5-methoxyphenyl)acetonitrile

HRID 885264Notes

Reaction equation

HRID 885264 reaction equation
[Br:1][C:2]1[CH:9]=[CH:8][C:7]([O:10][CH3:11])=[CH:6][C:3]=1[CH2:4]Br.[C-:12]#[N:13].[Na+].O.CCOC(C)=O>CS(C)=O>[Br:1][C:2]1[CH:9]=[CH:8][C:7]([O:10][CH3:11])=[CH:6][C:3]=1[CH2:4][C:12]#[N:13]

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 8929Sodium CyanideHCID 35259512-Bromo-5-methoxybenzyl bromide

Product 1

HCID 6396662-(2-Bromo-5-methoxyphenyl)acetonitrile

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
90 °C

Procedure

2-Bromo-5-methoxybenzyl bromide (2 g, 7.1 mmol) and sodium cyanide (0.526 g, 10.7 mmol) were combined in DMSO (20 mL) and heated to 90° C. for 3 hours. Once no starting material was seen by analytical tlc, the mixture was worked-up with H2O and EtOAc to give the desired product as a colorless oil.

Sources & evidence

ORD record
ord-d0793a1c9aaf43ea94f1b6e925b01d42
Source dataset
uspto-grants-2012_08
Patent number
US08242145B2

Reaction notes

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