Boron tribromide → 2-Fluoro-6-iodophenol

HRID 1581799

Reaction equation

HRID 1581799 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([I:8])[C:3]=1[O:9]C.B(Br)(Br)Br.C(=O)(O)[O-].[Na+]>ClCCl>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([I:8])[C:3]=1[OH:9]

Participants

5

Reactant 3

HCID 25134Boron tribromideHCID 516892Sodium BicarbonateHCID 227234331-Fluoro-3-iodo-2-methoxybenzene

Product 1

HCID 222374962-Fluoro-6-iodophenolYield 103.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 2-fluoro-6-iodoanisole (Justus Liebigs, Ann. Chem., 746:134, 1971; 4.31 g, 17.1 mmol) in dichloromethane (35 ml) is added a 1M solution of boron tribromide in dichloromethane (18.2 ml). The mixture is kept under argon and stirred for 4 hours at room temperature. The mixture is poured into a saturated aqueous sodium bicarbonate solution and the aqueous layer is extracted with ethyl acetate. The combined organic layers are dried over sodium sulfate and concentrated under reduced pressure to give 2-fluoro-6-iodophenol (4.2 g).

Workup

  1. extractionthe aqueous layer is extracted with ethyl acetate
  2. dry with materialThe combined organic layers are dried over sodium sulfate
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-f5aad8bdf73c43179351086bcd41f088
Source dataset
uspto-grants-2004_05
Patent number
US06730792B2

Linked notes

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