Benzonitrile, 4-bromo- → 4-(Furan-3-yl)benzonitrile

HRID 2299936Notes

Reaction equation

HRID 2299936 reaction equation
N1[CH:6]=[CH:5][C:4]([C:7]2[CH:11]=[CH:10][O:9][CH:8]=2)=[CH:3][CH:2]=1.BrC1C=C[C:16]([C:17]#[N:18])=CC=1.O1C=CC(B(O)O)=C1>>[C:17]([C:16]1[CH:6]=[CH:5][C:4]([C:7]2[CH:11]=[CH:10][O:9][CH:8]=2)=[CH:3][CH:2]=1)#[N:18]

Participants

4

Reactant 3

HCID 12162Benzonitrile, 4-bromo-HCID 2734358Furan-3-boronic acidHCID 108556024-(Furan-3-yl)pyridine

Product 1

HCID 116224004-(Furan-3-yl)benzonitrile

Procedure

As described in Example 1(d) for the preparation of 3-(pyridin 4-yl)furan, 4-bromobenzonitrile (4.00 g, 22.0 mmol) was coupled to 3-furanboronic acid to furnish in high yield crude 3-(4-cyanophenyl)-furan as a brown solid, mp 55-7° C., which was used immediately without further purification. 1H NMR (CDCl3): δ 7.82 (bs, 1H), 7.67 (d, 2H, J=8.4 Hz), 7.59 (d, 2H, J=8.4 Hz), 7.52 (t, 1H, J=1.9 Hz), 6.72 (bs, 1H). IR (KBr): 2214, 1608, 1160, 796 cm−1. Anal. Calculated for C11H7NO.0.1C6H6: C, 78.72; H, 4.33; N, 7.91. Found: C, 78.32; H, 4.60; N, 7.65.

Workup

  1. customto furnish

Sources & evidence

ORD record
ord-30a2c383be974b49a41bd1a5cb7fba8a
Source dataset
uspto-grants-2002_12
Patent number
US06495699B2

Reaction notes

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