Boron tribromide → 2-Chloro-6-fluorophenol

HRID 456438Notes

Reaction equation

HRID 456438 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[O:9]C.B(Br)(Br)Br>C(Cl)Cl>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[OH:9]

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 27735812-Chloro-6-fluoroanisole

Product 1

HCID 27737102-Chloro-6-fluorophenolYield 100.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-78 °C

Procedure

2-Chloro-6-fluoro anisole (5 g, 31.13 mmol) was dissolved in DCM (300 mL) and cooled to about −78° C. To the solution was added BBr3 (7.35 mL, 77.8 mmol) in one portion. The reaction was warmed to r.t, stirred for about 16 hours and poured over ice to quench remaining BBr3. The material was partitioned between water and DCM (500 mL each). The aqueous layer was back extracted with DCM (200 mL), and the combined organics were dried (NaSO4), filtered and concentrated to give the product (4.60 g) as a dark oil.

Workup

  1. temperatureThe reaction was warmed
  2. additionpoured over ice
  3. customto quench
  4. customThe material was partitioned between water and DCM (500 mL each)
  5. extractionThe aqueous layer was back extracted with DCM (200 mL)
  6. dry with materialthe combined organics were dried (NaSO4)
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-ea431b74c39c41f2b204465158176000
Source dataset
uspto-grants-2007_03
Patent number
US07186715B2

Reaction notes

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