(Z)-Prop-1-en-1-ylboronic acid → (Z)-2-nitro-6-(prop-1-enyl)benzonitrile

HRID 471602

Reaction equation

HRID 471602 reaction equation
FC(F)(F)S(O[C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([N+:13]([O-:15])=[O:14])[C:8]=1[C:16]#[N:17])(=O)=O.[CH:20](/B(O)O)=[CH:21]/[CH3:22]>>[N+:13]([C:9]1[CH:10]=[CH:11][CH:12]=[C:7](/[CH:20]=[CH:21]\[CH3:22])[C:8]=1[C:16]#[N:17])([O-:15])=[O:14]

Participants

3

Reactant 2

HCID 5355539(Z)-Prop-1-en-1-ylboronic acidHCID 866574732-Cyano-3-nitrophenyl trifluoromethanesulfonate

Product 1

HCID 67397071(Z)-2-nitro-6-(prop-1-enyl)benzonitrile

Procedure

Prepared as in Example 129c from 2-cyano-3-nitrophenyl trifluoromethanesulfonate Example (129d) and cis-1-propen-1-ylboronic acid. The crude product was purified by chromatography on silica gel eluting with solvent gradient 0% to 100% DCM in hexanes, to give 0.80 g (97%) of (Z)-2-nitro-6-(prop-1-enyl)benzonitrile (97%) as a yellow solid. 1H NMR (400 MHz, DMSO-d6) δ 8.25-8.30 (m, 1H), 7.90-7.98 (m, 2H), 6.25-6.70 (m, 1H), 6.17-6.28 (m, 1H), 1.78-1.82 (m, 3H).

Workup

  1. customThe crude product was purified by chromatography on silica gel eluting with solvent gradient 0% to 100% DCM in hexanes

Sources & evidence

ORD record
ord-90668f6716bb4efba03fff1f4b688774
Source dataset
uspto-grants-2014_01
Patent number
US08633186B2

Linked notes

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