Benzyl Bromide → 2-(Benzyloxy)-6-nitrobenzonitrile

HRID 711723Notes

Reaction equation

HRID 711723 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].C([O-])([O-])=O.[Cs+].[Cs+].[CH2:19](Br)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>CC(C)=O>[N+:10]([C:6]1[CH:7]=[CH:8][CH:9]=[C:2]([O:1][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:3]=1[C:4]#[N:5])([O-:12])=[O:11]

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 10796Cesium carbonateHCID 125032052-Hydroxy-6-nitrobenzonitrile

Product 1

HCID 203490242-(Benzyloxy)-6-nitrobenzonitrileYield 32.3%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of 2-hydroxy-6-nitrobenzonitrile (Example 115) (1.0 g, 6.09 mmol) and Cs2CO3 (2.16 g, 6.64 mmol) in acetone (14 mL) was added benzyl bromide (1.16 g, 6.76 mmol). The reaction was refluxed under N2 for 1.5 hours, then filtered and the filtrate concentrated. The residue was purified by flash chromatography 3:2 Hexane:EtOAc to provide 2-nitro-6-(benzyloxy)benzonitrile (500 mg, 32%). 1H NMR (400 MHz, MeOD) δ 5.40 (s, 2H), 7.34-7.45 (m, 3H), 7.53 (m, 2H), 7.69 (dd, J=8.6, 0.8 Hz, 1H), 7.82 (t, J=8.4 Hz, 1H), 7.91 (t, J=8.2, 0.8 Hz, 1H).

Workup

  1. temperatureThe reaction was refluxed under N2 for 1.5 hours
  2. filtrationfiltered
  3. concentrationthe filtrate concentrated
  4. customThe residue was purified by flash chromatography 3:2 Hexane

Sources & evidence

ORD record
ord-e518dd0bf85b4628b454d82c7f640e5d
Source dataset
uspto-grants-2015_11
Patent number
US09181276B2

Reaction notes

Loading…