Toluene → Methyl 6-(bicyclo[2.2.2]oct-5-ene-2-ylsulphonylmethyl)-3-bromo-2-methoxybenzoate

HRID 2177823Notes

Reaction equation

HRID 2177823 reaction equation
[Br:1][C:2]1[C:3]([O:18][CH3:19])=[C:4]([C:9]([CH2:12][S:13]([CH:16]=[CH2:17])(=[O:15])=[O:14])=[CH:10][CH:11]=1)[C:5]([O:7][CH3:8])=[O:6].C1CCC=CC=1.[C:26]1([CH3:32])[CH:31]=[CH:30]C=[CH:28][CH:27]=1>>[CH:17]12[CH2:30][CH2:31][CH:26]([CH:27]=[CH:28]1)[CH2:32][CH:16]2[S:13]([CH2:12][C:9]1[C:4]([C:5]([O:7][CH3:8])=[O:6])=[C:3]([O:18][CH3:19])[C:2]([Br:1])=[CH:11][CH:10]=1)(=[O:15])=[O:14]

Participants

4

Reactant 3

HCID 1140TolueneHCID 116051,3-CyclohexadieneHCID 67107909Methyl 3-bromo-2-methoxy-6-(vinylsulphonylmethyl)benzoate2×

Product 1

HCID 67107748Methyl 6-(bicyclo[2.2.2]oct-5-ene-2-ylsulphonylmethyl)-3-bromo-2-methoxybenzoate

Conditions

Temperature
125 °C

Procedure

A solution of methyl 3-bromo-2-methoxy-6-(vinylsulphonylmethyl)benzoate (Intermediate 172, 0.5 g), and cyclohexadiene (0.343 g) in toluene (0.5 ml) was sealed in a vial and heated at 125° C. for 3 days. After cooling, the mixture was evaporated to dryness and the residue was purified by chromatography on silica eluting with a mixture of ethyl acetate and cyclohexane with a gradient of 10-40% to give methyl 6-(bicyclo[2.2.2]oct-5-ene-2-ylsulphonylmethyl)-3-bromo-2-methoxybenzoate (0.455 g) as a white solid.

Workup

  1. temperatureAfter cooling
  2. customthe mixture was evaporated to dryness
  3. customthe residue was purified by chromatography on silica eluting with a mixture of ethyl acetate and cyclohexane with a gradient of 10-40%

Sources & evidence

ORD record
ord-c76281dd22574dc2a996cb700fb3bfdc
Source dataset
uspto-grants-2015_06
Patent number
US09067905B2

Reaction notes

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