Hydrogen Bromide → 4-Bromo-1-(3-methoxyphenyl)-1-(3-pyridinyl)-1-butene

HRID 1595226Notes

Reaction equation

HRID 1595226 reaction equation
[CH:1]1([C:4]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([O:18][CH3:19])[CH:13]=2)([C:6]2[CH:7]=[N:8][CH:9]=[CH:10][CH:11]=2)O)[CH2:3][CH2:2]1.[BrH:20].O.[OH-].[Na+]>C(O)(=O)C.C(OCC)(=O)C>[Br:20][CH2:3][CH2:2][CH:1]=[C:4]([C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([O:18][CH3:19])[CH:13]=1)[C:6]1[CH:7]=[N:8][CH:9]=[CH:10][CH:11]=1

Participants

7

Reactant 4

HCID 260Hydrogen BromideHCID 962WaterHCID 14798Sodium HydroxideHCID 15552043Cyclopropyl-(3-methoxyphenyl)-(3-pyridinyl)methanol

Product 1

HCID 538732124-Bromo-1-(3-methoxyphenyl)-1-(3-pyridinyl)-1-butene

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of the product of step 1 (470 mg) in acetic acid (5 ml) was added 48% aqueous HBr (3 ml) at 10° C. The reaction mixture was warmed to room temperature, and stirred for 12 hours. Water and ethyl acetate were added to the reaction mixture and neutralized with dilute NaOH solution. The organic layer was separated and washed with saturated aqueous sodium chloride, and dried over magnesium sulfate. The solvent was distilled off under reduced pressure. The residue was purified by silica gel chromatography eluting with ethyl acetate-hexane (1:4) to give 4-bromo-1-(3-methoxyphenyl)-1-(3-pyridinyl)-1-butene (560 mg).

Workup

  1. customThe organic layer was separated
  2. washwashed with saturated aqueous sodium chloride
  3. dry with materialdried over magnesium sulfate
  4. distillationThe solvent was distilled off under reduced pressure
  5. customThe residue was purified by silica gel chromatography
  6. washeluting with ethyl acetate-hexane (1:4)

Sources & evidence

ORD record
ord-05f9c931076044a0ad2f5559f25dfcbc
Source dataset
uspto-grants-2001_09
Patent number
US06288084B1

Reaction notes

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