Boron tribromide → HCID 14307650, compound

HRID 1165902Notes

Reaction equation

HRID 1165902 reaction equation
C[O:2][C:3]1[C:8]2[C:9]([CH3:19])=[C:10]([S:12][C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[O:11][C:7]=2[C:6]([O:20]C)=[C:5]([CH3:22])[C:4]=1[CH3:23].B(Br)(Br)Br>C(Cl)Cl>[C:13]1([S:12][C:10]2[O:11][C:7]3[C:6](=[O:20])[C:5]([CH3:22])=[C:4]([CH3:23])[C:3](=[O:2])[C:8]=3[C:9]=2[CH3:19])[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 14773540HCID 14773540, compound

Product 1

HCID 14307650HCID 14307650, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 4,7-dimethoxy-2-phenylthio3,5,6-trimethylbenzofuran from Step 2 (200 mg, 0.64 mmol) in CH2Cl2 (10 mL) was cooled to -78° C. and a BBr3 solution (2.8 mL, 2.8 mmol, 1M CH2Cl2) was added dropwise. The reaction was slowly warmed to room temperature then quenched with 25% NH4OAc. Extraction with EtOAc followed by addition of powdered FeCl3 and flash chromatography on silica gel (10% EtOAc/hex) afforded the title compound.

Workup

  1. customthen quenched with 25% NH4OAc
  2. extractionExtraction with EtOAc
  3. additionfollowed by addition of powdered FeCl3 and flash chromatography on silica gel (10% EtOAc/hex)

Sources & evidence

ORD record
ord-7fd5a3af8b524a519bba1827b0826596
Source dataset
uspto-grants-1990_03
Patent number
US04912131

Reaction notes

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