Boron tribromide → 3-Amino-2-chloro-4-fluorophenol

HRID 1771664Notes

Reaction equation

HRID 1771664 reaction equation
[Cl:1][C:2]1[C:8]([O:9]C)=[CH:7][CH:6]=[C:5]([F:11])[C:3]=1[NH2:4].B(Br)(Br)Br.C([O-])(O)=O.[Na+]>C(Cl)Cl>[NH2:4][C:3]1[C:2]([Cl:1])=[C:8]([OH:9])[CH:7]=[CH:6][C:5]=1[F:11]

Participants

5

Reactant 3

HCID 25134Boron tribromideHCID 516892Sodium BicarbonateHCID 184447472-Chloro-6-fluoro-3-methoxyaniline

Product 1

HCID 216600263-Amino-2-chloro-4-fluorophenolYield 95%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-chloro-6-fluoro-3-methoxy-aniline (0.85 g, 4.84 mmol, 1.0 eq) in DCM (8 mL) at 0° C. was added BBr3 (6.06 g, 24.2 mmol, 5.0 eq). The mixture was stirred at room temperature under N2 overnight, then poured into ice-water. The pH of the solution was adjusted to pH 6 by addition of sat.NaHCO3. The dichloromethane was removed under reduced pressure and the aqueous residue was extracted with EtOAc. The combined organic extracts were washed with brine, dried (Na2SO4), filtered and evaporated in vacuo to give the title compound as a pale yellow solid (0.74 g, 95%).

Workup

  1. additionThe pH of the solution was adjusted to pH 6 by addition
  2. customThe dichloromethane was removed under reduced pressure
  3. extractionthe aqueous residue was extracted with EtOAc
  4. washThe combined organic extracts were washed with brine
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. customevaporated in vacuo

Sources & evidence

ORD record
ord-75f2b7f7b4bd4bf2b7e379593e098b82
Source dataset
uspto-grants-2016_02
Patent number
US09249085B2

Reaction notes

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