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

HRID 1967720Notes

Reaction equation

HRID 1967720 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:10])=[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]([CH3:10])=[C:6]([CH:7]([OH:8])[CH2:12][C:11]#[N:13])[CH:9]=1

Participants

3

Reactant 2

HCID 6342AcetonitrileHCID 104202895-Bromo-2-methylbenzaldehyde

Product 1

HCID 666292453-(5-Bromo-2-methylphenyl)-3-hydroxypropanenitrile

Procedure

Alkylation of 5-bromo-2-methylbenzaldehyde with acetonitrile following the method used in Example 114 gave 3-(5-bromo-2-methylphenyl)-3-hydroxypropanenitrile as a pale yellow oil. Yield (3.33 g, 86%): 1H NMR (400 MHz, DMSO-d6) δ 7.61 (d, J=2.0 Hz, 1H), 7.35 (dd, J=8.0, 2.0 Hz, 1H), 7.09 (d, J=8.0 Hz, 1H), 5.96 (d, J=4.4 Hz, 1H), 5.04-5.00 (m, 1H), 2.88 (ABd, J=16.8, 4.4 Hz, 1H), 2.77 (ABd, J=16.8, 6.4 Hz, 1H), 2.23 (s, 3H).

Sources & evidence

ORD record
ord-7e40fc83f0bb4523b66a8586adf1dbf5
Source dataset
uspto-grants-2013_04
Patent number
US08420863B2

Reaction notes

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