Water → 6-[(1E)-3-Bromo-1-(4-tert-butylphenyl)prop-1-en-1-yl]-3-chloro-2-methoxypyridine

HRID 70527Notes

Reaction equation

HRID 70527 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:20]([Br:24])(Br)(Br)Br.[C:25]([C:29]1[CH:34]=[CH:33][C:32](/[C:35](/[C:39]2[CH:44]=[CH:43][C:42]([Cl:45])=[C:41]([O:46][CH3:47])[N:40]=2)=[CH:36]\CO)=[CH:31][CH:30]=1)([CH3:28])([CH3:27])[CH3:26].O>O1CCCC1>[Br:24][CH2:20]/[CH:36]=[C:35](/[C:39]1[N:40]=[C:41]([O:46][CH3:47])[C:42]([Cl:45])=[CH:43][CH:44]=1)\[C:32]1[CH:31]=[CH:30][C:29]([C:25]([CH3:28])([CH3:26])[CH3:27])=[CH:34][CH:33]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 58452849(2E)-3-(4-tert-Butylphenyl)-3-(5-chloro-6-methoxypyridin-2-yl)prop-2-en-1-ol

Product 1

HCID 584528146-[(1E)-3-Bromo-1-(4-tert-butylphenyl)prop-1-en-1-yl]-3-chloro-2-methoxypyridineYield 118%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Triphenylphosphine (1.10 g) and carbon tetrabromide (1.81 g) were sequentially added to a solution of (2E)-3-(4-tert-butylphenyl)-3-(5-chloro-6-methoxypyridin-2-yl)prop-2-en-1-ol (912 mg) in tetrahydrofuran (30 mL) under ice-cooling, and the mixture was stirred under ice-cooling for 1.5 hours. Water was added to the reaction solution, followed by extraction with ethyl acetate. The organic layer was washed with brine and dried over sodium sulfate. After filtration, the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=9:1) to give the title compound as a black powder (1.28 g).

Workup

  1. temperaturecooling
  2. temperaturecooling for 1.5 hours
  3. extractionfollowed by extraction with ethyl acetate
  4. washThe organic layer was washed with brine
  5. dry with materialdried over sodium sulfate
  6. filtrationAfter filtration
  7. customthe solvent was evaporated under reduced pressure
  8. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=9:1)

Sources & evidence

ORD record
ord-18ef660aedce4bbfac9ee852553e6f87
Source dataset
uspto-grants-2014_09
Patent number
US08822503B2

Reaction notes

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