Triethylamine → 3-Nitro-5-(2-trimethylsilylvinyl)benzoic acid methyl ester

HRID 1280135Notes

Reaction equation

HRID 1280135 reaction equation
[CH3:1][O:2][C:3](=[O:14])[C:4]1[CH:9]=[C:8]([N+:10]([O-:12])=[O:11])[CH:7]=[C:6](I)[CH:5]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(N(CC)CC)C.[CH:41]([Si:43]([CH3:46])([CH3:45])[CH3:44])=[CH2:42]>C(#N)C.CC([O-])=O.CC([O-])=O.[Pd+2].[N+]([O-])([O-])=O.[Ag+]>[CH3:1][O:2][C:3](=[O:14])[C:4]1[CH:5]=[C:6]([CH:42]=[CH:41][Si:43]([CH3:46])([CH3:45])[CH3:44])[CH:7]=[C:8]([N+:10]([O-:12])=[O:11])[CH:9]=1

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 11776TriphenylphosphineHCID 79102VinyltrimethylsilaneHCID 7020599Methyl 3-iodo-5-nitrobenzoate

Product 1

HCID 543670333-Nitro-5-(2-trimethylsilylvinyl)benzoic acid methyl ester

Reagents, catalysts & solvents 3

HCID 24470Silver NitrateCatalystHCID 167845palladium(II) acetateCatalystHCID 6342AcetonitrileSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 3-iodo-5-nitrobenzoic acid methyl ester (307 mg, 1.0 mmol), Pd(OAc)2 (67 mg, 0.30 mmol), triphenylphosphine (0.032 g, 0.60 mmol), AgNO3 (170 mg, 1.0 mmol), triethylamine (0.167 ml, 1.2 mmol) and vinyltrimethylsilane (0.309 ml, 2.0 mmol) was dissolved in acetonitrile (10 ml) and the solution was heated to 60° C. in a closed vessel for 48 h. The precipitated salts were filtered off and the filtrate was evaporated. The residue was chromatographed on silica gel using a mixture of ethyl acetate and heptane (1:11) as the eluent. Yield: 210 mg (75%).

Workup

  1. filtrationThe precipitated salts were filtered off
  2. customthe filtrate was evaporated
  3. customThe residue was chromatographed on silica gel using
  4. additiona mixture of ethyl acetate and heptane (1:11) as the eluent

Sources & evidence

ORD record
ord-3ec028b86a564582b165988a5b4a41e0
Source dataset
uspto-grants-2002_09
Patent number
US06448442B1

Reaction notes

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