Tributylvinyltin → Benzene, 4-ethenyl-2-nitro-1-(phenylmethoxy)-

HRID 1373756Notes

Reaction equation

HRID 1373756 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12](Br)=[CH:11][C:10]=1[N+:16]([O-:18])=[O:17])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:19]([Sn](CCCC)(CCCC)C=C)[CH2:20]CC>CN(C=O)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[N+:16]([C:10]1[CH:11]=[C:12]([CH:19]=[CH2:20])[CH:13]=[CH:14][C:9]=1[O:8][CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)([O-:18])=[O:17]

Participants

5

Reactant 2

HCID 81998TributylvinyltinHCID 112782421-(Benzyloxy)-4-bromo-2-nitrobenzene

Product 1

HCID 11253842Benzene, 4-ethenyl-2-nitro-1-(phenylmethoxy)-Yield 94%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 6228DimethylformamideSolvent

Procedure

A mixture of Example 68A (2.18 g, 7.08 mmol), Pd(PPh3)4 (1.23 g, 1.06 mmol) and tributyl-vinyl-stannane (2.48 mL, 8.49 mmol) in DMF (200 mL) was heated at 80° C. overnight. The solvent was removed by vacuum pump. The residue was dissolved in acetone (50 mL), and dried with silica gel powder (20 g). 10% ethyl acetate in hexanes (2 L) was used to run flash chromatography to give the title compound (1.69 g, 94%). MS (DCI) m/z 273.03 (M+NH4)+; 1H NMR (500 MHz, CD2Cl2) δ ppm 5.23 (s, 2 H) 5.72 (d, J=17.47 Hz, 1 H) 6.67 (dd, J=17.78, 10.92 Hz, 1 H) 7.12 (d, J=8.73 Hz, 1 H) 7.35 (m, 1 H) 7.38–7.43 (m, 2 H) 7.44–7.48 (m, 2 H) 7.56 (dd, J=8.73, 2.18 Hz, 1 H) 7.87 (d, J=2.18 Hz, 1 H).

Workup

  1. customThe solvent was removed by vacuum pump
  2. dissolutionThe residue was dissolved in acetone (50 mL)
  3. customdried with silica gel powder (20 g)

Sources & evidence

ORD record
ord-4ca7dd57565f4c3f9263ecdcc3466702
Source dataset
uspto-grants-2007_01
Patent number
US07163939B2

Reaction notes

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