Boron tribromide → 4-Chloro-5-fluoro-2-methyl-quinolin-8-ol

HRID 1959549Notes

Reaction equation

HRID 1959549 reaction equation
[Cl:1][C:2]1[C:11]2[C:6](=[C:7]([O:13]C)[CH:8]=[CH:9][C:10]=2[F:12])[N:5]=[C:4]([CH3:15])[CH:3]=1.B(Br)(Br)Br>C1(C)C=CC=CC=1.C(Cl)Cl>[Cl:1][C:2]1[C:11]2[C:6](=[C:7]([OH:13])[CH:8]=[CH:9][C:10]=2[F:12])[N:5]=[C:4]([CH3:15])[CH:3]=1

Participants

5

Reactant 2

HCID 25134Boron tribromideHCID 684232214-Chloro-5-fluoro-8-methoxy-2-methyl-quinoline

Product 1

HCID 670774504-Chloro-5-fluoro-2-methyl-quinolin-8-ol

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6344DichloromethaneSolvent

Procedure

4-Chloro-5-fluoro-8-methoxy-2-methyl-quinoline (0.440 g, 1.95 mmol) was coevaporated in anhydrous toluene (2×15 mL). The residue was dissolved in anhydrous DCM (25 mL) and BBr3 (1 M in DCM, 9.8 mL, 9.8 mmol) was added dropwise at −75° C. The reaction mixture was allowed to warm to room temperature over 3.5 h. The reaction mixture was then concentrated in vacuo and the residue was partitioned between DCM (10 mL) and water (7 mL). The pH of the aqueous layer was adjusted to 8 by the addition of saturated aqueous NaHCO3 solution and the aqueous layer was extracted with DCM (2×30 mL). The combined organic layers were dried over Na2SO4, filtered, and concentrated in vacuo to give the title compound. MS (m/z): 212.3 [M+H+].

Workup

  1. concentrationThe reaction mixture was then concentrated in vacuo
  2. customthe residue was partitioned between DCM (10 mL) and water (7 mL)
  3. additionThe pH of the aqueous layer was adjusted to 8 by the addition of saturated aqueous NaHCO3 solution
  4. extractionthe aqueous layer was extracted with DCM (2×30 mL)
  5. dry with materialThe combined organic layers were dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-d42726b52d7043f0803d705fedeb0d41
Source dataset
uspto-grants-2013_04
Patent number
US08410134B2

Reaction notes

Loading…