Acetonitrile → HCID 66629194, compound

HRID 1967724Notes

Reaction equation

HRID 1967724 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[F:10])[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]=[CH:8][C:9]=1[F:10]

Participants

3

Reactant 2

HCID 6342AcetonitrileHCID 1736043-Bromo-4-fluorobenzaldehyde

Product 1

HCID 66629194HCID 66629194, compound

Procedure

Alkylation of 3-bromo-4-fluorobenzaldehyde with acetonitrile following the method used in Example 115 gave 3-(3-bromo-4-fluorophenyl)-3-hydroxypropanenitrile as a pale yellow oil. Yield (4.2 g, 70%): 1H NMR (400 MHz, DMSO-d6) δ 7.71 (dd, J=6.8, 2.0 Hz, 1H), 7.44 (ddd, J=8.4, 5.2, 2.4 Hz, 1H), 7.35 (t, J=8.8 Hz, 1H), 6.08 (bs, 1H), 4.90 (s, 1H), 2.90 (ABd, J=16.8, 5.2 Hz, 1H), 2.83 (ABd, J=16.8, 6.4 Hz, 1H).

Sources & evidence

ORD record
ord-e1f8b2e6aacf4e749607c8994c993b79
Source dataset
uspto-grants-2013_04
Patent number
US08420863B2

Reaction notes

Loading…