Boron tribromide → [4-(1-Benzyl-piperidine-2-ylmethoxy)-phenyl]-[6-hydroxy-2-(4-hydroxy-phenyl)-benzo[b]thiophen-3-yl]-methanone

HRID 354087Notes

Reaction equation

HRID 354087 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][CH2:11][CH2:10][CH:9]1[CH2:14][O:15][C:16]1[CH:21]=[CH:20][C:19]([C:22]([C:24]2[C:25]3[CH:40]=[CH:39][C:38]([O:41]C)=[CH:37][C:26]=3[S:27][C:28]=2[C:29]2[CH:34]=[CH:33][C:32]([O:35]C)=[CH:31][CH:30]=2)=[O:23])=[CH:18][CH:17]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.B(Br)(Br)Br>C(Cl)Cl>[CH2:1]([N:8]1[CH2:13][CH2:12][CH2:11][CH2:10][CH:9]1[CH2:14][O:15][C:16]1[CH:17]=[CH:18][C:19]([C:22]([C:24]2[C:25]3[CH:40]=[CH:39][C:38]([OH:41])=[CH:37][C:26]=3[S:27][C:28]=2[C:29]2[CH:30]=[CH:31][C:32]([OH:35])=[CH:33][CH:34]=2)=[O:23])=[CH:20][CH:21]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 23512907[4-(1-Benzyl-piperidine-2-ylmethoxy)-phenyl]-[6-methoxy-2-(4-methoxy-phenyl)-benzo[b]thiophen-3-yl]-methanone

Product 1

HCID 12992343[4-(1-Benzyl-piperidine-2-ylmethoxy)-phenyl]-[6-hydroxy-2-(4-hydroxy-phenyl)-benzo[b]thiophen-3-yl]-methanone

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The product from Step 3 (295 mg, 0.5 mmol) was combined with boron tribromide (2.50 mL, 1M in dichloromethane, 2.5 mmol) in 4 mL of methylene chloride at room temperature. After 2 hours the reaction was quenched with saturated sodium bicarbonate solution and extracted into chloroform-methanol (10: 1). The combined organic layers was washed with brine and dried over anhydrous magnesium sulfate. After filtration, concentration and silica gel column chromatography with 40% ethyl acetate-hexanes as eluant the title compound (169 mg) was obtained.

Workup

  1. customAfter 2 hours the reaction was quenched with saturated sodium bicarbonate solution
  2. extractionextracted into chloroform-methanol (10: 1)
  3. washThe combined organic layers was washed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationAfter filtration, concentration and silica gel column chromatography with 40% ethyl acetate-hexanes as eluant the title compound (169 mg)
  6. customwas obtained

Sources & evidence

ORD record
ord-089b0cab4fef45188f170379488086ce
Source dataset
uspto-grants-2004_06
Patent number
US06756388B1

Reaction notes

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