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

HRID 628651Notes

Reaction equation

HRID 628651 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([F:10])[CH:9]=1)[CH:5]=[O:6].[C:11](#[N:13])[CH3:12]>>[Br:1][C:2]1[CH:3]=[C:4]([CH:5]([OH:6])[CH2:12][C:11]#[N:13])[CH:7]=[C:8]([F:10])[CH:9]=1

Participants

3

Reactant 2

HCID 6342AcetonitrileHCID 219862463-Bromo-5-fluorobenzaldehyde

Product 1

HCID 689405323-(3-Bromo-5-fluorophenyl)-3-hydroxypropanenitrile

Procedure

Alkylation of 3-bromo-5-fluorobenzaldehyde with acetonitrile following the method used in Example 50 except KOBu-t was used instead of LDA gave 3-(3-bromo-5-fluorophenyl)-3-hydroxypropanenitrile as a light color oil. Yield (2.5 g, 86%): NMR (400 MHz, CDCl3) δ 7.34 (bs, 1H), 7.21-7.24 (m, 1H), 7.08-7.11 (m, 1H), 5.02 (t, J=6.4 Hz, 1H), 2.75 (d, J=6.4 Hz, 2H).

Sources & evidence

ORD record
ord-7661fd0a7c7d455b9c3ad364b5d4bc3c
Source dataset
uspto-grants-2016_04
Patent number
US09314467B2

Reaction notes

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