Carbon tetrabromide → HCID 67972772, compound

HRID 445113Notes

Reaction equation

HRID 445113 reaction equation
[CH3:1][C:2]1[C:7]([C:8]2[CH:9]=[C:10]([CH2:14]O)[CH:11]=[CH:12][CH:13]=2)=[C:6]([CH3:16])[CH:5]=[C:4]([O:17][CH2:18][CH2:19][CH2:20][S:21]([CH3:24])(=[O:23])=[O:22])[N:3]=1.C(Br)(Br)(Br)[Br:26].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C(Cl)Cl>[Br:26][CH2:14][C:10]1[CH:9]=[C:8]([C:7]2[C:2]([CH3:1])=[N:3][C:4]([O:17][CH2:18][CH2:19][CH2:20][S:21]([CH3:24])(=[O:23])=[O:22])=[CH:5][C:6]=2[CH3:16])[CH:13]=[CH:12][CH:11]=1

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 67972773HCID 67972773, compound

Product 1

HCID 67972772HCID 67972772, compoundYield 59.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

[3-[2,4-dimethyl-6-(3-methylsulfonylpropoxy)pyridin-3-yl]phenyl]methanol (0.30 g) synthesized according to the methods in (Reference Example 5) and (Example 11) <Step 2> and carbon tetrabromide (0.34 g) were dissolved in methylene chloride (1.8 mL) and to the resultant solution, a solution of triphenylphosphine (0.34 g) in methylene chloride (0.9 mL) was added, followed by stirring the resultant reaction mixture at room temperature for 3 hours. From the reaction mixture, the solvent was distilled off under reduced pressure, and the resultant residue was purified by silica gel column chromatography (eluate; n-hexane:ethyl acetate=3:2) to obtain the subject compound (0.21 g) as a colorless liquid.

Workup

  1. customreaction mixture at room temperature for 3 hours
  2. distillationFrom the reaction mixture, the solvent was distilled off under reduced pressure
  3. customthe resultant residue was purified by silica gel column chromatography (eluate; n-hexane:ethyl acetate=3:2)

Sources & evidence

ORD record
ord-1962238a7b7e4f3da76e9855d90fa27b
Source dataset
uspto-grants-2013_07
Patent number
US08476287B2

Reaction notes

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