Boron tribromide → 2-(2,6-Difluorophenyl)quinazolin-8-ol

HRID 408475Notes

Reaction equation

HRID 408475 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[C:9]1[N:18]=[CH:17][C:16]2[C:11](=[C:12]([O:19]C)[CH:13]=[CH:14][CH:15]=2)[N:10]=1.B(Br)(Br)Br>C(Cl)Cl>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[C:9]1[N:18]=[CH:17][C:16]2[C:11](=[C:12]([OH:19])[CH:13]=[CH:14][CH:15]=2)[N:10]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 583868032-(2,6-Difluorophenyl)-8-methoxyquinazoline

Product 1

HCID 583867962-(2,6-Difluorophenyl)quinazolin-8-olYield 94%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of the 2-(2,6-difluorophenyl)-8-methoxyquinazoline (1.0 eq) in methylene chloride (0.23M) was added BBr3 (2.0 eq) at room temperature. The reaction mixture was stirred overnight. The solvents were removed under reduced pressure. The residue was dissolved in ethyl acetate (150 mL), and washed with NaHCO3, brine, then dried over MgSO4, filtered, and evaporated under reduced pressure to give crude product, which was purified by column (ethyl acetate:hexanes=1:2) to yield 2-(2,6-difluorophenyl)quinazolin-8-ol (94%). LC/MS (m/z): 259.0 (MH+), Rt=0.82.

Workup

  1. customThe solvents were removed under reduced pressure
  2. dissolutionThe residue was dissolved in ethyl acetate (150 mL)
  3. washwashed with NaHCO3, brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customevaporated under reduced pressure
  7. customto give crude product, which
  8. customwas purified by column (ethyl acetate:hexanes=1:2)

Sources & evidence

ORD record
ord-532747dbe8c44802847063e830eda47c
Source dataset
uspto-grants-2014_06
Patent number
US08759338B2

Reaction notes

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