2-Bromopropane → 2-Nitro-6-isopropoxybenzonitrile

HRID 711722Notes

Reaction equation

HRID 711722 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][CH:7]=[C:6]([N+:10]([O-:12])=[O:11])[C:3]=1[C:4]#[N:5].[CH:13](Br)([CH3:15])[CH3:14]>>[N+:10]([C:6]1[CH:7]=[CH:8][CH:9]=[C:2]([O:1][CH:13]([CH3:15])[CH3:14])[C:3]=1[C:4]#[N:5])([O-:12])=[O:11]

Participants

3

Reactant 2

HCID 63582-BromopropaneHCID 125032052-Hydroxy-6-nitrobenzonitrile

Product 1

HCID 127157832-Nitro-6-isopropoxybenzonitrileYield 64%

Procedure

Prepared in a similar manner as Example 115c from 2-hydroxy-6-nitrobenzonitrile (Example 115d) and isopropyl bromide to provide 2-nitro-6-isopropoxybenzonitrile (324 mg, 64%). 1H NMR (400 MHz, MeOD) δ 1.43 (d, J=6.2 Hz, 6H), 4.89 (sept, J=6.2 Hz, 1H), 7.61 (dd, J=8.0, 1.0 Hz, 1H), 7.80 (t, J=8.2 Hz, 1H), 7.85 (dd, J=8.2, 1.2 Hz, 1H).

Sources & evidence

ORD record
ord-58e14679d79c48458ae3fc3e86c1b4d1
Source dataset
uspto-grants-2015_11
Patent number
US09181276B2

Reaction notes

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