Boron tribromide → 2-Bromo-3-fluorophenol

HRID 456437Notes

Reaction equation

HRID 456437 reaction equation
[Br:1][C:2]1[C:7]([F:8])=[CH:6][CH:5]=[CH:4][C:3]=1[O:9]C.B(Br)(Br)Br>C(Cl)Cl>[Br:1][C:2]1[C:7]([F:8])=[CH:6][CH:5]=[CH:4][C:3]=1[OH:9]

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 27793182-Bromo-3-fluoroanisole

Product 1

HCID 121757012-Bromo-3-fluorophenolYield 100.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-78 °C

Procedure

2-Bromo-3-fluoro anisole (10 g, 48.77 mmol) was dissolved in DCM (200 mL) and cooled to about −78° C. To the solution was added BBr3 (11.53 mL, 121.9 mmol) in one portion. The mixture was warmed to r.t. and stirred overnight. The mixture was partitioned between water and DCM (50 mL), and the aqueous layer was back extracted with DCM (200 mL). The combined organics were dried (NaSO4), filtered and concentrated to give about 9.32 g of the product as a dark oil. MS found 188.9 (M−1)

Workup

  1. temperatureThe mixture was warmed to r.t.
  2. customThe mixture was partitioned between water and DCM (50 mL)
  3. extractionthe aqueous layer was back extracted with DCM (200 mL)
  4. dry with materialThe combined organics were dried (NaSO4)
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-54439269130d44049780b801b96807af
Source dataset
uspto-grants-2007_03
Patent number
US07186715B2

Reaction notes

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