Triphenylphosphine → 5-Bromo-3-((1R)-1-(2,6-dichloro-3-fluorophenyl)ethoxy)-2-nitropyridine

HRID 1845853Notes

Reaction equation

HRID 1845853 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C.[Cl:34][C:35]1[C:40]([F:41])=[CH:39][CH:38]=[C:37]([Cl:42])[C:36]=1[C@@H:43]([OH:45])[CH3:44].[Br:46][C:47]1[CH:48]=[C:49](O)[C:50]([N+:53]([O-:55])=[O:54])=[N:51][CH:52]=1>C1COCC1>[Br:46][C:47]1[CH:48]=[C:49]([O:45][C@@H:43]([C:36]2[C:37]([Cl:42])=[CH:38][CH:39]=[C:40]([F:41])[C:35]=2[Cl:34])[CH3:44])[C:50]([N+:53]([O-:55])=[O:54])=[N:51][CH:52]=1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 5363146Diisopropyl azodicarboxylateHCID 11557536(S)-1-(2,6-dichloro-3-fluorophenyl)ethanolHCID 534184205-Bromo-2-nitropyridin-3-ol

Product 1

HCID 681943985-Bromo-3-((1R)-1-(2,6-dichloro-3-fluorophenyl)ethoxy)-2-nitropyridineYield 99.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirred solution of triphenyl phosphine (9.4 g, 0.036 mol) and DIAD (7.2 g. 0.036 mol) in THF (100 mL) at 0° C. was added a solution of (S)-1-(2,6-dichloro-3-fluorophenyl)ethanol (4.55 g, 0.021 mol) and 5-bromo-3-hydroxy-2-nitropyridine (3.35 g, 0.023 mol) in THF (200 mL). The resulting bright orange solution was stirred under a nitrogen atmosphere at ambient temperature for 4 hours at which point all starting materials had been consumed. The solvent was removed, and the crude material was dry loaded onto silica gel, and eluted with ethyl acetate-hexanes (20:80) to yield the title compound as a white solid (8.6 g, 85%).

Workup

  1. customhad been consumed
  2. customThe solvent was removed
  3. dry with materialthe crude material was dry
  4. washeluted with ethyl acetate-hexanes (20:80)

Sources & evidence

ORD record
ord-79d933b157f3440db3be1ec737f0a211
Source dataset
uspto-grants-2015_02
Patent number
US08951993B2

Reaction notes

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