Carbon tetrabromide → HCID 18769618, compound

HRID 1048491Notes

Reaction equation

HRID 1048491 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH:7](O)[CH2:8][CH2:9][CH3:10].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(Br)(Br)(Br)[Br:32]>C1COCC1>[Br:32][CH:7]([C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=1)[CH2:8][CH2:9][CH3:10]

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 13926171HCID 13926171, compound

Product 1

HCID 18769618HCID 18769618, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a mixture of 1-(pyridin-2-yl)butan-1-ol (0.35 g, 2.3 mmol; Example 231, Step A) and triphenylphosphine (1.1 g, 4.2 mmol) in THF (15 mL) at 0° C. under N2 atmosphere was added CBr4 (1.2 g, 3.5 mmol). The mixture was stirred at 0° C. for 2 min, and then was allowed to warm to rt and stirred for 25 min. The precipitate was filtered off through a pad of Celite® (J.T. Baker, Phillipsberg, N.J., diatomaceous earth), the solid was washed with cold THF (10 mL). The filtrate was concentrated under reduced pressure. Purification of the residue by flash chromatography on silica gel with 0-5-15% EtOAc/Hexanes provided the title compound as colorless oil. Mass Spectrum (ESI) m/z=214.0 and 216.0 (M+1).

Workup

  1. temperatureto warm to rt
  2. stirringstirred for 25 min
  3. filtrationThe precipitate was filtered off through a pad of Celite® (J.T. Baker, Phillipsberg, N.J., diatomaceous earth)
  4. washthe solid was washed with cold THF (10 mL)
  5. concentrationThe filtrate was concentrated under reduced pressure
  6. customPurification of the residue by flash chromatography on silica gel with 0-5-15% EtOAc/Hexanes

Sources & evidence

ORD record
ord-0881855a3cc9420084aa8a78e75b07e8
Source dataset
uspto-grants-2013_10
Patent number
US08569341B2

Reaction notes

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