Carbon tetrabromide → HCID 18769618, compound

HRID 932177Notes

Reaction equation

HRID 932177 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-1c926c903c3b476f94f456b9898636dd
Source dataset
uspto-grants-2016_03
Patent number
US09296736B2

Reaction notes

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