Boron tribromide → HCID 23296312, compound

HRID 1455906Notes

Reaction equation

HRID 1455906 reaction equation
[ClH:1].C[O:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[S:14][C:13]3[CH:15]=[C:16]([O:19]C)[CH:17]=[CH:18][C:12]=3[C:11]=2[C:21]2[CH:26]=[CH:25][CH:24]=[C:23]([O:27][CH2:28][CH2:29][N:30]3[CH2:35][CH2:34][CH2:33][CH2:32][CH2:31]3)[CH:22]=2)=[CH:6][CH:5]=1.B(Br)(Br)Br>ClCl>[ClH:1].[OH:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[S:14][C:13]3[CH:15]=[C:16]([OH:19])[CH:17]=[CH:18][C:12]=3[C:11]=2[C:21]2[CH:26]=[CH:25][CH:24]=[C:23]([O:27][CH2:28][CH2:29][N:30]3[CH2:31][CH2:32][CH2:33][CH2:34][CH2:35]3)[CH:22]=2)=[CH:6][CH:5]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 23296319HCID 23296319, compound

Product 1

HCID 23296312HCID 23296312, compound

Reagents, catalysts & solvents 1

HCID 24526ChlorineSolvent

Conditions

Temperature
0 °C

Procedure

2-(4-Methoxyphenyl)-3-[3-[2-(1-piperidinyl)ethoxy]phenyl]-6-methoxybenzo[b]thiophene hydrochloride, 2 g (4 mmol) was dissolved in 125 mL of CH2 Cl2 and cooled to 0+ C. 1.0 mL (10 mmol) of BBr3 was added and the reaction mixture was stirred at 0° C. for 3 hours under a nitrogen atmosphere. The reaction was quenched by pouring into a mixture of 125 mL of aqueous NaHCO3, 25 mL of isopropanol, and 250 mL of CHCl3. The organic layer was separated and washed twice with brine, dried with Na2SO4, and evaporated to dryness. The resulting solid was re-dissolved in 150 mL of EtOAc and dry HCl gas was bubbled through. The solvents were removed by evaporation. This yielded 850 mg of the title compound as a white powder.

Workup

  1. temperaturecooled to 0+ C
  2. customThe reaction was quenched
  3. additionby pouring into a mixture of 125 mL of aqueous NaHCO3, 25 mL of isopropanol, and 250 mL of CHCl3
  4. customThe organic layer was separated
  5. washwashed twice with brine
  6. dry with materialdried with Na2SO4
  7. customevaporated to dryness
  8. dissolutionThe resulting solid was re-dissolved in 150 mL of EtOAc
  9. customdry HCl gas was bubbled through
  10. customThe solvents were removed by evaporation

Sources & evidence

ORD record
ord-bfa15adf558b432c9232fbcfa0c41f44
Source dataset
uspto-grants-1998_12
Patent number
US05843940

Reaction notes

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