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

HRID 1484162Notes

Reaction equation

HRID 1484162 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([Cl:10])[CH:5]=[C:6]([CH:9]=1)[CH:7]=[O:8].[C:11](#[N:13])[CH3:12]>>[Br:1][C:2]1[CH:3]=[C:4]([Cl:10])[CH:5]=[C:6]([CH:7]([OH:8])[CH2:12][C:11]#[N:13])[CH:9]=1

Participants

3

Reactant 2

HCID 6342AcetonitrileHCID 177509523-Bromo-5-chlorobenzaldehyde

Product 1

HCID 666295203-(3-Bromo-5-chlorophenyl)-3-hydroxypropanenitrile

Procedure

Alkylation of 5-bromo-3-chlorobenzaldehyde with acetonitrile following the method used in Example 115 gave 3-(5-bromo-3-chlorophenyl)-3-hydroxypropanenitrile as a clear oil. Yield (3.21 g, 54%): 1H NMR (400 MHz, DMSO-d6) δ 7.62 (t, J=2.0 Hz, 1H), 7.58-7.57 (m, 1H), 7.49-4.48 (m, 1H), 6.18 (d, J=4.8 Hz, 1H), 4.93-4.90 (m, 1H), 2.93 (ABd, J=16.8, 5.2 Hz, 1H), 2.86 (ABd, J=17.2, 6.8 Hz, 1H).

Sources & evidence

ORD record
ord-1c32ce2e7f8f44b88137f91c458f115a
Source dataset
uspto-grants-2016_08
Patent number
US09421210B2

Reaction notes

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