Boron tribromide → [6-Hydroxy-2-(4-hydroxyphenyl)-1-benzothiophen-3-YL](4-methoxyphenyl)methanone

HRID 1274271Notes

Reaction equation

HRID 1274271 reaction equation
C[O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[S:13][C:12]3[CH:14]=[C:15]([O:18]C)[CH:16]=[CH:17][C:11]=3[C:10]=2[C:20](=[O:29])[C:21]2[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[CH:23][CH:22]=2)=[CH:5][CH:4]=1.B(Br)(Br)Br>C(Cl)(Cl)Cl>[OH:2][C:3]1[CH:4]=[CH:5][C:6]([C:9]2[S:13][C:12]3[CH:14]=[C:15]([OH:18])[CH:16]=[CH:17][C:11]=3[C:10]=2[C:20](=[O:29])[C:21]2[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[CH:23][CH:22]=2)=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 9953060LY88074 Trimethyl ether

Product 1

HCID 9842621[6-Hydroxy-2-(4-hydroxyphenyl)-1-benzothiophen-3-YL](4-methoxyphenyl)methanoneYield 11.8%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
10 °C

Procedure

2-(4-Methoxyphenyl)-3-(4-methoxybenzoyl)-6-methoxybenzo[b]thiophene (53 g, 131 mmol) was dissolved in chloroform and cooled to 10° C. To this stirring mixture was added boron tribromide (75 g, 296 mmol) and the reaction was allowed to proceed for twenty-four hours at ambient temperature. The reaction was terminated by pouring into water. The organic layer was separated, filtered, and evaporated to dryness. The residue was dissolved in benzene, filtered, and evaporated to dryness. The crude product was further purified by chromatography on a silica gel column eluting with diethylether-benzene (9:1) and then rechromatographed on alumina eluting with diethylether followed by a methanol-ether (1:9) wash and evaporation of the solvents to yield 5.8 g of the title compound. mp 138° C.-140° C. EA calculated for C22H16O4S: C, 70.20; H, 4.28; O, 17.00. Found: C, 70.46; H, 4.50; O, 16.87.

Workup

  1. waitto proceed for twenty-four hours at ambient temperature
  2. customThe reaction was terminated
  3. additionby pouring into water
  4. customThe organic layer was separated
  5. filtrationfiltered
  6. customevaporated to dryness
  7. dissolutionThe residue was dissolved in benzene
  8. filtrationfiltered
  9. customevaporated to dryness
  10. customThe crude product was further purified by chromatography on a silica gel column
  11. washeluting with diethylether-benzene (9:1)
  12. customrechromatographed on alumina eluting with diethylether
  13. washwash
  14. customevaporation of the solvents

Sources & evidence

ORD record
ord-adf982da51824a1c9ba085b708c2d0ab
Source dataset
uspto-grants-2000_12
Patent number
US06156786

Reaction notes

Loading…