Acetonitrile → 3-(3-Bromo-5-methoxyphenyl)-3-hydroxypropanenitrile

HRID 242755Notes

Reaction equation

HRID 242755 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([O:10][CH3:11])[CH:9]=1)[CH:5]=[O:6].[C:12](#[N:14])[CH3:13]>>[Br:1][C:2]1[CH:3]=[C:4]([CH:5]([OH:6])[CH2:13][C:12]#[N:14])[CH:7]=[C:8]([O:10][CH3:11])[CH:9]=1

Participants

3

Reactant 2

HCID 6342AcetonitrileHCID 106086983-Bromo-5-methoxybenzaldehyde

Product 1

HCID 666286853-(3-Bromo-5-methoxyphenyl)-3-hydroxypropanenitrile

Procedure

Alkylation of 3-bromo-5-methoxybenzaldehyde with acetonitrile following the method used in Example 115 gave 3-(3-bromo-5-methoxyphenyl)-3-hydroxypropanenitrile as a pale yellow oil. Yield (4.1 g, 70%): 1H NMR (400 MHz, DMSO-d6) δ 7.16-7.15 (m, 1H), 7.04-7.03 (m, 1H), 6.97-6.96 (m, 1H), 6.04 (d, J=4.8 Hz, 1H), 4.87-4.83 (m, 1H), 3.74 (s, 3H), 2.89 (ABd, J=16.4, 5.2 Hz, 1H), 2.81 (ABd, J=16.8, 6.8 Hz, 1H).

Sources & evidence

ORD record
ord-aeeb7acb77384a8e8c14d830352ef84f
Source dataset
uspto-grants-2014_02
Patent number
US08653142B2

Reaction notes

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