Tin tetrachloride → HCID 18944331, compound

HRID 400198Notes

Reaction equation

HRID 400198 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[CH:10]=[C:9]([C:11]3[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][CH:12]=3)[S:8][C:7]=2[CH:19]=1.[Br:20][C:21]1[CH:29]=[CH:28][C:24]([C:25](Cl)=[O:26])=[CH:23][CH:22]=1.[Sn](Cl)(Cl)(Cl)Cl>C(Cl)Cl>[Br:20][C:21]1[CH:29]=[CH:28][C:24]([C:25]([C:10]2[C:6]3[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:19][C:7]=3[S:8][C:9]=2[C:11]2[CH:12]=[CH:13][C:14]([O:17][CH3:18])=[CH:15][CH:16]=2)=[O:26])=[CH:23][CH:22]=1

Participants

5

Reactant 3

HCID 24287Tin tetrachlorideHCID 685154-Bromobenzoyl chlorideHCID 8509416-Methoxy-2-(4-methoxyphenyl)benzo[b]thiophene

Product 1

HCID 18944331HCID 18944331, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 0.54 g (2 mmol) of 6-methoxy-2-(4-methoxyphenyl)benzo-[b]thiophene and 0.52 g (2.3 mmol) of 4-bromobenzoyl chloride in 20 mL of methylene chloride at 0° C. was added dropwise a solution of 0.3 ml (2.5 mmol) of tin (IV) chloride in 5 mL of methylene chloride. After stirring for 16 hours the solution was concentrated and the residue was washed with aqueous sodium bicarbonate and extracted 2 times with 40 mL of ethyl acetate. The organic layers were combined, dried (MgSO4) and concentrated. The crude solid was passed through a short plug of silica gel to remove residual tin salts. Elution with 30% EtOAc:hexane and concentration yielded 0.65 g (73%) of yellow crystals, m.p. 127°-129° C.

Workup

  1. concentrationwas concentrated
  2. washthe residue was washed with aqueous sodium bicarbonate
  3. extractionextracted 2 times with 40 mL of ethyl acetate
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated
  6. customto remove residual tin salts
  7. washElution with 30% EtOAc
  8. concentrationhexane and concentration

Sources & evidence

ORD record
ord-e1ecbfb660574bc3adfb623be5fb79b8
Source dataset
uspto-grants-1998_10
Patent number
US05827876

Reaction notes

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