Boron tribromide → HCID 67004506, compound

HRID 1513854Notes

Reaction equation

HRID 1513854 reaction equation
[ClH:1].[F:2][C:3]1[CH:8]=[CH:7][C:6]([F:9])=[CH:5][C:4]=1[C:10]1[CH:19]=[CH:18][C:17]2[C:12](=[CH:13][CH:14]=[C:15]([O:20]C)[CH:16]=2)[C:11]=1[O:22][C:23]1[CH:37]=[CH:36][C:26]([O:27][CH2:28][CH2:29][N:30]2[CH2:35][CH2:34][CH2:33][CH2:32][CH2:31]2)=[CH:25][CH:24]=1.B(Br)(Br)Br>ClCCl>[ClH:1].[F:2][C:3]1[CH:8]=[CH:7][C:6]([F:9])=[CH:5][C:4]=1[C:10]1[C:11]([O:22][C:23]2[CH:37]=[CH:36][C:26]([O:27][CH2:28][CH2:29][N:30]3[CH2:35][CH2:34][CH2:33][CH2:32][CH2:31]3)=[CH:25][CH:24]=2)=[C:12]2[C:17](=[CH:18][CH:19]=1)[CH:16]=[C:15]([OH:20])[CH:14]=[CH:13]2

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 67004613HCID 67004613, compound

Product 1

HCID 67004506HCID 67004506, compoundYield 84.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Dissolve 1-(2-{4-[2-(2,5-difluoro-phenyl)-6-methoxy-naphthalen-1-yloxy]-phenoxy}-ethyl)-piperidine hydrochloride (133 mg, 0.25 mmol) in dichloromethane (5 ml), cool in an ice bath and add boron tribromide (1M in dichloromethane, 0.76 mL, 0.76 mmol). Let slowly warm to ambient temperature over 18 hours, quench with saturated aqueous solution of sodium bicarbonate, dry organic layer with magnesium sulfate, filter and chromatograph on silica gel with dichloromethane/methanol mixtures. Combine fractions containing product, add 1M hydrogen chloride in ether (1 mL) and remove solvent under vacuum to give 108 mg (83%) of the title compound: mass spectrum (ion spray) m/z=476 (M−Cl).

Workup

  1. temperaturecool in an ice bath
  2. customquench with saturated aqueous solution of sodium bicarbonate, dry organic layer with magnesium sulfate
  3. filtrationfilter
  4. additionCombine fractions containing product
  5. additionadd 1M hydrogen chloride in ether (1 mL)
  6. customremove solvent under vacuum

Sources & evidence

ORD record
ord-51afd9f3bfde4c4eb30c396328b1c87a
Source dataset
uspto-grants-2012_07
Patent number
US08217032B2

Reaction notes

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