Boron tribromide → 3-(6-(Dibenzo[b,d]thiophen-4-yl)pyridin-2-yl)phenol

HRID 385312Notes

Reaction equation

HRID 385312 reaction equation
[CH:1]1[C:9]2[C:8]3[CH:10]=[CH:11][CH:12]=[CH:13][C:7]=3[S:6][C:5]=2[C:4]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([C:20]3[CH:25]=[CH:24][CH:23]=[C:22]([O:26]C)[CH:21]=3)[N:15]=2)=[CH:3][CH:2]=1.B(Br)(Br)Br>ClCCl>[CH:1]1[C:9]2[C:8]3[CH:10]=[CH:11][CH:12]=[CH:13][C:7]=3[S:6][C:5]=2[C:4]([C:14]2[N:15]=[C:16]([C:20]3[CH:21]=[C:22]([OH:26])[CH:23]=[CH:24][CH:25]=3)[CH:17]=[CH:18][CH:19]=2)=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 594892612-(Dibenzo[b,d]thiophen-4-yl)-6-(3-methoxyphenyl)pyridine

Product 1

HCID 594892693-(6-(Dibenzo[b,d]thiophen-4-yl)pyridin-2-yl)phenolYield 11%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

2-(dibenzo[b,d]thiophen-4-yl)-6-(3-methoxyphenyl)pyridine (3.8 g, 103 mmol) was dissolved in 120 mL dichloromethane. The solution was cooled to 0° C. under nitrogen. BBr3 (22.8 mL, 1M in hexane) was slowly added in at 0° C. and then was slowly brought up to room temperature. The mixture was stirred at room temperature overnight. A brown solid was observed to form. The reaction was quenched by adding 100 mL water slowly. The dichloromethane was removed by rotovap. Then the mixture was refluxed for three hours. Saturated sodium bicarbonate solution was added to neutralize the mixture, which was extracted by dichloromethane and ethyl acetate. The combined organic layers were dried over magnesium sulfate, filtered and concentrated under reduced pressure to obtain 4 gram glassy dark brown solid. The product was used for next step without further purification.

Workup

  1. customwas slowly brought up to room temperature
  2. customto form
  3. customThe reaction was quenched
  4. additionby adding 100 mL water slowly
  5. customThe dichloromethane was removed by rotovap
  6. temperatureThen the mixture was refluxed for three hours
  7. additionSaturated sodium bicarbonate solution was added
  8. extractionwas extracted by dichloromethane and ethyl acetate
  9. dry with materialThe combined organic layers were dried over magnesium sulfate
  10. filtrationfiltered
  11. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-6464b9aeb44346a8b64c3e1240b159e6
Source dataset
uspto-grants-2013_02
Patent number
US08367850B2

Reaction notes

Loading…