Triethylamine → Methyl 3-bromo-2-methoxy-6-(vinylsulphonylmethyl)benzoate

HRID 2177824Notes

Reaction equation

HRID 2177824 reaction equation
[Br:1][C:2]1[C:3]([O:19][CH3:20])=[C:4]([C:9]([CH2:12][S:13]([CH2:16][CH2:17]O)(=[O:15])=[O:14])=[CH:10][CH:11]=1)[C:5]([O:7][CH3:8])=[O:6].CS(Cl)(=O)=O.C(N(CC)CC)C>C(Cl)Cl>[Br:1][C:2]1[C:3]([O:19][CH3:20])=[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]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 67107820Methyl 3-bromo-6-(2-hydroxyethanesulphonylmethyl)-2-methoxybenzoate2×

Product 1

HCID 67107909Methyl 3-bromo-2-methoxy-6-(vinylsulphonylmethyl)benzoateYield 80.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Methyl 3-bromo-6-(2-hydroxyethanesulphonylmethyl)-2-methoxybenzoate (Intermediate 173, 0.68 g) and methanesulphonyl chloride (0.424 g) were added to a solution of triethylamine (0.561 g) in DCM (10 ml) and the resultant mixture was stirred in an ice bath for 1 hour. DCM was added and the solution was washed with water, dried (Na2SO4) and filtered. The filtrate 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 3-bromo-2-methoxy-6-(vinylsulphonylmethyl)benzoate (0.521 g) as a colourless gum which crystallized on standing to a white solid.

Workup

  1. washthe solution was washed with water
  2. dry with materialdried (Na2SO4)
  3. filtrationfiltered
  4. customThe filtrate was evaporated to dryness
  5. customthe residue was purified by chromatography on silica
  6. washeluting with a mixture of ethyl acetate and cyclohexane with a gradient of 10-40%

Sources & evidence

ORD record
ord-eccc25653eb8416a9d6237cd060c2aaf
Source dataset
uspto-grants-2015_06
Patent number
US09067905B2

Reaction notes

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