Sodium Bicarbonate → 2-Fluoro-6-iodophenol

HRID 1272198

Reaction equation

HRID 1272198 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([I:8])[C:3]=1[O:9]C.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

4

Reactant 2

HCID 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 borontribromide 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 extracts 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 extracts are dried over sodium sulfate
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-7aae7ab989e2411ba518f92aa7752415
Source dataset
uspto-grants-2007_04
Patent number
US07208505B2

Linked notes

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