Iodine → Methyl 3-chloro-6-methylbenzo(b)thiophene-2-carboxylate

HRID 962751Notes

Reaction equation

HRID 962751 reaction equation
[CH3:1][C:2]1[CH:3]=[CH:4][C:5]2[C:9]([Cl:10])=[C:8]([C:11](Cl)=[O:12])[S:7][C:6]=2[CH:14]=1.[CH3:15][OH:16].Cl[Si](C)(C)C.II>C(OCC)(=O)C.CCCCCC>[CH3:1][C:2]1[CH:3]=[CH:4][C:5]2[C:9]([Cl:10])=[C:8]([C:11]([O:16][CH3:15])=[O:12])[S:7][C:6]=2[CH:14]=1

Participants

7

Reactant 4

HCID 807IodineHCID 887MethanolHCID 6397ChlorotrimethylsilaneHCID 123398623-Chloro-6-methylbenzo(b)thiophene-2-carbonyl chloride

Product 1

HCID 4154210Methyl 3-chloro-6-methylbenzo(b)thiophene-2-carboxylate

Reagents, catalysts & solvents 2

HCID 8058HexaneSolventHCID 8857Ethyl AcetateSolvent2×

Procedure

Crude 6-methyl-3-chlorobenzo[b]thiophene-2-carbonyl chloride (5 g, 20.46 mmoles) was transferred to a 250 ml round bottomed flask. Anhydrous methanol (Aldrich, 80 ml) was added and the acid chloride dissolved by stirring. To this stirred solution was added chlorotrimethylsilane (3.0 equivalents, 61.38 mmole, 6.68 g, 7.80 ml). The reaction mixture was stirred at room temperature and the progress of the reaction monitored by TLC (Silica, 1:1 hexane:ethyl acetate, and 100% ethyl acetate, iodine and UV visualization). The reaction was shown to be complete after 24 hours. The resulting slurry was concentrated in vacuo to give 4.80 g of a yellow solid, which was shown by 1H NMR (DMSO-D6, 400 MHz) to be the desired material. The crude methyl ester was shown to be pure and used directly.

Workup

  1. stirringThe reaction mixture was stirred at room temperature
  2. concentrationThe resulting slurry was concentrated in vacuo

Sources & evidence

ORD record
ord-0b780b1be62a439992aa285a745662cd
Source dataset
uspto-grants-1998_06
Patent number
US05760062

Reaction notes

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