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

HRID 471586Notes

Reaction equation

HRID 471586 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-baa2cabc85c9464b99363ef6dda6e976
Source dataset
uspto-grants-2014_01
Patent number
US08633186B2

Reaction notes

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