Carbon tetrabromide → HCID 58105214, compound

HRID 1172251Notes

Reaction equation

HRID 1172251 reaction equation
O[CH2:2][C:3]1[N:8]=[C:7]([CH2:9][CH2:10][C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH:6]=[CH:5][CH:4]=1.C(Br)(Br)(Br)[Br:19].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C(Cl)Cl>[Br:19][CH2:2][C:3]1[N:8]=[C:7]([CH2:9][CH2:10][C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH:6]=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 58105238HCID 58105238, compound

Product 1

HCID 58105214HCID 58105214, compoundYield 69.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

t-Butyl 3-(6-hydroxymethylpyridin-2-yl)propionate (16.13 g) was dissolved in 200 mL of dry methylene chloride, and 33.8 g of carbon tetrabromide was added to the above solution, additionally 21.5 g of triphenylphosphine was added thereto in small portions under stirring at ice temperature, and then the mixture was stirred at the same temperature for 30 minutes. The reaction mixture was transferred to a separating funnel, washed with saturated aqueous sodium bicarbonate, then brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. To the residue, 200 mL of a mixture of hexane-ethyl acetate (2:1) was added, the insoluble portion precipitated was filtrated off, and the filtrate was concentrated under reduced pressure. The residue was purified by chromatography on silica gel (hexane-ethyl acetate=5:1) to give 14.12 g of t-butyl 3-(6-bromomethylpyridin-2-yl)propionate as a light yellow oil.

Workup

  1. additionwas added
  2. stirringthe mixture was stirred at the same temperature for 30 minutes
  3. customThe reaction mixture was transferred to a separating funnel
  4. washwashed with saturated aqueous sodium bicarbonate
  5. dry with materialbrine, dried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. additionTo the residue, 200 mL of a mixture of hexane-ethyl acetate (2:1) was added
  8. customthe insoluble portion precipitated
  9. filtrationwas filtrated off
  10. concentrationthe filtrate was concentrated under reduced pressure
  11. customThe residue was purified by chromatography on silica gel (hexane-ethyl acetate=5:1)

Sources & evidence

ORD record
ord-2235894ab77d4f4d98f4b773b7a72fd0
Source dataset
uspto-grants-2010_11
Patent number
US07834002B2

Reaction notes

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