1,8-Diazabicyclo(5.4.0)undec-7-ene → 3-Bromo-4-(2-chloro-5-fluorophenoxy)pyridine

HRID 1046009Notes

Reaction equation

HRID 1046009 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[OH:9].[Br:10][C:11]1[CH:12]=[N:13][CH:14]=[CH:15][C:16]=1Cl.C1CCN2C(=NCCC2)CC1>CN1C(=O)CCC1>[Br:10][C:11]1[CH:12]=[N:13][CH:14]=[CH:15][C:16]=1[O:9][C:3]1[CH:4]=[C:5]([F:8])[CH:6]=[CH:7][C:2]=1[Cl:1]

Participants

5

Reactant 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 8176963-Bromo-4-chloropyridineHCID 27245222-Chloro-5-fluorophenol

Product 1

HCID 674666933-Bromo-4-(2-chloro-5-fluorophenoxy)pyridineYield 84%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

A mixture of 2-chloro-5-fluorophenol (1.50 g, 10.24 mmol), 3-bromo-4-chloropyridine (1.50 g, 7.79 mmol) and DBU (1.50 g, 9.85 mmol) were heated at 130° C. in NMP (10 mL) for 15 hours. The reaction mixture was cooled and partitioned between water (100 mL) and MTBE (100 mL). The organic layer was separated, washed with dilute aq NaOH and brine, dried (MgSO4) and concentrated in vacuo to provide 3-bromo-4-(2-chloro-5-fluorophenoxy)pyridine (1.98 g, 84% yield) as brownish oil suitable for use in the next reaction. MS (ESI) m/z: 303.9 (M+H+).

Workup

  1. temperatureThe reaction mixture was cooled
  2. custompartitioned between water (100 mL) and MTBE (100 mL)
  3. customThe organic layer was separated
  4. washwashed with dilute aq NaOH and brine
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-8ce7acec63df48f3ac58a9d011b3e58e
Source dataset
uspto-grants-2013_10
Patent number
US08569319B2

Reaction notes

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