Acetonitrile → 3-(5-Bromo-2-chlorophenyl)-3-hydroxypropanenitrile

HRID 628656Notes

Reaction equation

HRID 628656 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([Cl:10])=[C:6]([CH:9]=1)[CH:7]=[O:8].[C:11](#[N:13])[CH3:12]>>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([Cl:10])=[C:6]([CH:7]([OH:8])[CH2:12][C:11]#[N:13])[CH:9]=1

Participants

3

Reactant 2

HCID 6342AcetonitrileHCID 106089255-Bromo-2-chlorobenzaldehyde

Product 1

HCID 666293653-(5-Bromo-2-chlorophenyl)-3-hydroxypropanenitrile

Procedure

Alkylation of 5-bromo-2-chlorobenzaldehyde with acetonitrile following the method used in Example 114 gave 3-(5-bromo-2-chlorophenyl)-3-hydroxypropanenitrile as a pale yellow liquid. Yield (4.42 g, 75%): 1H NMR (400 MHz, DMSO-d6) δ 7.74 (d, J=2.8 Hz, 1H), 7.53 (dd, J=8.8, 2.8 Hz, 1H), 7.39 (d, J=8.8 Hz, 1H), 6.30 (d, J=4.8 Hz, 1H), 5.13-5.09 (m, 1H), 2.96 (ABd, J=16.8, 4.8 Hz, 1H), 2.83 (ABd, J=17.0, 6.0 Hz, 1H).

Sources & evidence

ORD record
ord-b189518737924c0d914a31bdd6822510
Source dataset
uspto-grants-2016_04
Patent number
US09314467B2

Reaction notes

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