Dichloromethane → HCID 87491517, compound

HRID 2243480Notes

Reaction equation

HRID 2243480 reaction equation
[CH3:1][O:2][C:3]([C:5]1[C:6]2[CH:14]=[CH:13][C:12]([Cl:15])=[CH:11][C:7]=2[S:8][C:9]=1[OH:10])=[O:4].C(Cl)Cl.[O:19](S(C(F)(F)F)(=O)=O)[S:20]([C:23]([F:26])([F:25])[F:24])(=O)=[O:21]>CCN(CC)CC>[CH3:1][O:2][C:3]([C:5]1[C:6]2[CH:14]=[CH:13][C:12]([Cl:15])=[CH:11][C:7]=2[S:8][C:9]=1[O:10][S:20]([C:23]([F:26])([F:25])[F:24])(=[O:21])=[O:19])=[O:4]

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 67749Trifluoromethanesulfonic anhydrideHCID 68547613HCID 68547613, compound

Product 1

HCID 87491517HCID 87491517, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

6-chloro-2-hydroxy-benzo[b]thiophene-3-carboxylic acid methyl ester (2.46 g, 10.1 mmol) was cooled to 0° C. in a solution of DCM (25 ml) and Et3N (25 ml). Tf2O (2.56 ml, 15.2 mmol, 1.5 equiv) was added dropwise, then stirred for 1 hr. The resulting solution was washed twice with water, saturated NaHCO3, then water, followed by drying over MgSO4. This was filtered and the solvent removed in vacuo. The crude material was purified by column chromatography leaving 2.61 g (68%) of 6-chloro-2-trifluoromethanesulfonyloxy-benzo[b]thiophene-3-carboxylic acid methyl ester as a white solid.

Workup

  1. washThe resulting solution was washed twice with water, saturated NaHCO3
  2. dry with materialby drying over MgSO4
  3. filtrationThis was filtered
  4. customthe solvent removed in vacuo
  5. customThe crude material was purified by column chromatography

Sources & evidence

ORD record
ord-620bc8c58c444e858f82418d4f28dae7
Source dataset
uspto-grants-2010_03
Patent number
US07674822B2

Reaction notes

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