Acetonitrile → 3-(3-Bromophenyl)-3-hydroxypropanenitrile

HRID 1967715Notes

Reaction equation

HRID 1967715 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH:5]=[O:6].[C:10](#[N:12])[CH3:11]>>[Br:1][C:2]1[CH:3]=[C:4]([CH:5]([OH:6])[CH2:11][C:10]#[N:12])[CH:7]=[CH:8][CH:9]=1

Participants

3

Reactant 2

HCID 6342AcetonitrileHCID 765833-Bromobenzaldehyde

Product 1

HCID 576083633-(3-Bromophenyl)-3-hydroxypropanenitrile

Procedure

Alkylation of 3-bromobenzaldehyde with acetonitrile following the method described in Example 50 gave 3-(3-bromophenyl)-3-hydroxypropanenitrile as a light yellow oil. Yield (2.75 g, 81%): 1H NMR (400 MHz, DMSO-d6) δ 7.60 (t, J=1.6 Hz, 1H), 7.46 (ddd, J=7.6, 2.0, 1.2 Hz, 1H), 7.40 (dd, J=7.6, 2.0 Hz, 1H), 7.31 (t, J=7.6 Hz, 1H), 6.05 (d, J=4.8 Hz, 1H), 2.94-2.80 (m, 2H).

Sources & evidence

ORD record
ord-ada58dc670194428ae3877da555d1fc4
Source dataset
uspto-grants-2013_04
Patent number
US08420863B2

Reaction notes

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