Chloroform → 3-Bromo-2-(4-methoxyphenyl)benzo[b]thiophene

HRID 367248Notes

Reaction equation

HRID 367248 reaction equation
[Br:1][C:2]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[S:4][C:3]=1Br.[CH3:12][O:13][C:14]1[CH:19]=[CH:18][C:17](B(O)O)=[CH:16][CH:15]=1.C([O-])([O-])=O.[Na+].[Na+].C(Cl)(Cl)Cl>C1COCC1.CCOC(C)=O.C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C>[CH3:12][O:13][C:14]1[CH:19]=[CH:18][C:17]([C:3]2[S:4][C:5]3[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=3[C:2]=2[Br:1])=[CH:16][CH:15]=1

Participants

8

Reactant 4

HCID 6212ChloroformHCID 10340Sodium CarbonateHCID 949772,3-Dibromo-1-benzothiopheneHCID 201262(4-Methoxyphenyl)boronic acid

Product 1

HCID 105436263-Bromo-2-(4-methoxyphenyl)benzo[b]thiopheneYield 78%

Reagents, catalysts & solvents 3

HCID 80271Tri-o-tolylphosphineCatalystHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of the dibromobenzothiophene (11 g, 37.7 mmol), p-methoxyphenylboronic acid (5.7 g, 37.7 mmol), Pd(OAc) to (58 mg, 0.26 mmol) and tri-ortho-tolyl phosphine (237 mg) in 38 mL THF was treated with 38 mL 2 M Na2CO3 and refluxed in the absence of light overnight. Diluted with 100 mL EtOAc and separated the layers. The aqueous layer was extracted with EtOAc (50 mL). The combined organic layer was dried over MgSO4 and concentrated to an oil which was purified by chromatography (SiO2 ; stepwise 5 then 8% CHCl3 in hexanes) to recover 9.34 g (29.3 mmol, 78%) of the desired compound as a white solid.

Workup

  1. temperaturerefluxed in the absence of light overnight
  2. customseparated the layers
  3. extractionThe aqueous layer was extracted with EtOAc (50 mL)
  4. dry with materialThe combined organic layer was dried over MgSO4
  5. concentrationconcentrated to an oil which
  6. customwas purified by chromatography (SiO2

Sources & evidence

ORD record
ord-fbca36e1c17b431f9f961d09fc2e5e9f
Source dataset
uspto-grants-2000_10
Patent number
US06133262

Reaction notes

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