Boron tribromide → HCID 59191211, compound

HRID 1023899Notes

Reaction equation

HRID 1023899 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([O:8][C:9]2[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][CH3:17])=[CH:11][C:10]=2[O:18]C)[N:3]=1.B(Br)(Br)Br.[NH4+].[Cl-]>ClCCl>[F:1][C:2]1[N:3]=[C:4]([O:8][C:9]2[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][CH3:17])=[CH:11][C:10]=2[OH:18])[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 25134Boron tribromideHCID 25517Ammonium ChlorideHCID 59191318HCID 59191318, compound

Product 1

HCID 59191211HCID 59191211, compoundYield 38.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-fluoro-6-(2-methoxy-4-propylphenoxy)pyridine (1.7 mmol; 449 mg) under argon, in dichloromethane (1.5 mL), cooled to −78° C., was added BBr3 (17 mmol; 1M in CH2Cl2; 17 mL). The reaction mixture was allowed to stir overnight, with gradual heating to room temperature. At −20° C., the reaction was hydrolysed with saturated NH4Cl (3 mL), extracted with ethyl acetate (3*10 mL). Combined organic phases were dried over MgSO4, concentrated in vacuo. The residue was chromatographed on silica gel (gradient cyclohexane/dichloromethane) to give the desired product as a white solid (160 mg; 0.65 mmol; 38%).

Workup

  1. customAt −20° C.
  2. extractionextracted with ethyl acetate (3*10 mL)
  3. dry with materialCombined organic phases were dried over MgSO4
  4. concentrationconcentrated in vacuo
  5. customThe residue was chromatographed on silica gel (gradient cyclohexane/dichloromethane)

Sources & evidence

ORD record
ord-8d48dda7d7bf4c54b0ae40bc7df5bf3c
Source dataset
uspto-grants-2014_05
Patent number
US08722746B2

Reaction notes

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