Triphenylphosphine → 1-(3-Bromo-4-{[(4-chloro-2-pyridinyl)methyl]oxy}phenyl)ethanone

HRID 879992Notes

Reaction equation

HRID 879992 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([CH2:8][OH:9])[CH:3]=1.[Br:10][C:11]1[CH:12]=[C:13]([C:18](=[O:20])[CH3:19])[CH:14]=[CH:15][C:16]=1O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCOC(/N=N/C(OCC)=O)=O>C1COCC1>[Br:10][C:11]1[CH:12]=[C:13]([C:18](=[O:20])[CH3:19])[CH:14]=[CH:15][C:16]=1[O:9][CH2:8][C:4]1[CH:3]=[C:2]([Cl:1])[CH:7]=[CH:6][N:5]=1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 6080941-(3-Bromo-4-hydroxyphenyl)ethanoneHCID 2763167(4-Chloropyridin-2-yl)methanolHCID 5462977Diethyl azodicarboxylate

Product 1

HCID 682019601-(3-Bromo-4-{[(4-chloro-2-pyridinyl)methyl]oxy}phenyl)ethanone

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of (4-chloro-2-pyridinyl)methanol (Commercial eg Aldrich) (0.2 g) in THF (5 ml) were added 1-(3-bromo-4-hydroxyphenyl)ethanone (0.3 g) and triphenylphosphine (0.547 g). This was stirred for 10 min before cooling and adding slowly DEAD (0.363 g). This was stirred for 16 h. The reaction mixture was partitioned between water and ethyl acetate. The aqueous was reextracted with ethyl acetate and the combined organics were washed with brine, dried over sodium sulfate and concentrated in vacuo. This was purified through silica eluting with 0-35% ethyl acetate in hexane to give the title compound, 0.30 g

Workup

  1. temperaturebefore cooling
  2. stirringThis was stirred for 16 h
  3. customThe reaction mixture was partitioned between water and ethyl acetate
  4. washthe combined organics were washed with brine
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated in vacuo
  7. customThis was purified through silica eluting with 0-35% ethyl acetate in hexane

Sources & evidence

ORD record
ord-0afcd3a3bfe04c7e9f8e70e335a340dd
Source dataset
uspto-grants-2015_03
Patent number
US08993560B2

Reaction notes

Loading…