Chlorosulfonic acid → (7-Chlorosulfonyl-6-methoxy-benzo[b]thiophen-3-yl)-acetic acid ethyl ester

HRID 1727057Notes

Reaction equation

HRID 1727057 reaction equation
[CH2:1]([O:3][C:4](=[O:17])[CH2:5][C:6]1[C:7]2[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[CH:11][C:8]=2[S:9][CH:10]=1)[CH3:2].[Cl:18][S:19](O)(=[O:21])=[O:20]>C(Cl)Cl>[CH2:1]([O:3][C:4](=[O:17])[CH2:5][C:6]1[C:7]2[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[C:11]([S:19]([Cl:18])(=[O:21])=[O:20])[C:8]=2[S:9][CH:10]=1)[CH3:2]

Participants

4

Reactant 2

HCID 24638Chlorosulfonic acidHCID 21816275Ethyl 2-(6-methoxybenzo[b]thiophen-3-yl)acetate

Product 1

HCID 57565234(7-Chlorosulfonyl-6-methoxy-benzo[b]thiophen-3-yl)-acetic acid ethyl esterYield 3.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of compound from step 2 (1.0 g, 4.0 mmol) in CH2Cl2 (10 mL) was added chlorosulfonic acid (0.56 mL, 8.0 mmol). The resulting mixture was stirred for 4 hours at room temperature. The solvent was evaporated in vacuo and the residue was dissolved in EtOAc. The solution was washed with Na2CO3, brine and dried over Na2SO4. Evaporation of solvent afforded 50 mg of desired compound. 1H NMR (400 MHz, CDCl3) δ 8.08 (d, 1H), 7.38 (s, 1H), 6.90 (d, 1H), 4.21 (q, 2H), 4.02 (s, 2H), 4.01 (s, 3H), 1.24 (t, 3H).

Workup

  1. customThe solvent was evaporated in vacuo
  2. dissolutionthe residue was dissolved in EtOAc
  3. washThe solution was washed with Na2CO3, brine
  4. dry with materialdried over Na2SO4
  5. customEvaporation of solvent

Sources & evidence

ORD record
ord-1eb809e3fa9942ab90664e8e4e3e8c5e
Source dataset
uspto-grants-2009_02
Patent number
US07494999B2

Reaction notes

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