Boron tribromide → 4-Chloro-2-iodophenol

HRID 2356609Notes

Reaction equation

HRID 2356609 reaction equation
B(Br)(Br)Br.[Cl:5][C:6]1[CH:11]=[CH:10][C:9]([O:12]C)=[C:8]([I:14])[CH:7]=1>ClCCl>[Cl:5][C:6]1[CH:11]=[CH:10][C:9]([OH:12])=[C:8]([I:14])[CH:7]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 28009784-Chloro-2-iodoanisole

Product 1

HCID 6202344-Chloro-2-iodophenolYield 99.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

109.4 g (0.436 mol) of boron tribromide were added over 10 minutes to a stirred solution of 90 g (0.335 mol) of 4-chloro-2-iodoanisole in dichloromethane (900 ml) at −78° C. under nitrogen. Cooling was removed and allowed to warm to room temperature and stirred for 5 hours. Poured onto ice and diluted with a further 800 ml of water. The organic phase was separated, the aqueous extracted with dichloromethane and the combined organics washed with saturated sodium bicarbonate, dried and evaporated to give 84.87 g of off-white solid.

Workup

  1. temperatureCooling
  2. customwas removed
  3. additionPoured onto ice
  4. additiondiluted with a further 800 ml of water
  5. customThe organic phase was separated
  6. extractionthe aqueous extracted with dichloromethane
  7. washthe combined organics washed with saturated sodium bicarbonate
  8. customdried
  9. customevaporated

Sources & evidence

ORD record
ord-1f6b324eb554486d9ef9675794b9a148
Source dataset
uspto-grants-2010_07
Patent number
US07759369B2

Reaction notes

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