Water → HCID 16125382, compound

HRID 239874Notes

Reaction equation

HRID 239874 reaction equation
[F:1][C:2]1[C:9]([O:10]C)=[CH:8][CH:7]=[C:6]([I:12])[C:3]=1[C:4]#[N:5].B(Br)(Br)Br.O>ClCCl>[F:1][C:2]1[C:9]([OH:10])=[CH:8][CH:7]=[C:6]([I:12])[C:3]=1[C:4]#[N:5]

Participants

5

Reactant 3

HCID 962WaterHCID 25134Boron tribromideHCID 16124903HCID 16124903, compound

Product 1

HCID 16125382HCID 16125382, compoundYield 78.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A −78° C. solution of 2-fluoro-6-iodo-3-methoxybenzonitrile (148 mg, 0.53 mmol) in dichloromethane (5 mL) was treated dropwise with BBr3 (2.5 mL, 1M in dichloromethane, 2.5 mmol), warmed to room temperature, stirred for 18 hours, poured into water, and extracted with diethyl ether. The extract was dried (MgSO4), filtered, and concentrated. The residue was purified by flash column chromatography on silica gel with 20% ethyl acetate/hexanes to provide 110 mg of the desired product. MS (ESI(−)) m/e 262 (M−H)−.

Workup

  1. extractionextracted with diethyl ether
  2. dry with materialThe extract was dried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue was purified by flash column chromatography on silica gel with 20% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-5aaa72278e9b42e2815a6cbdb5e2a79a
Source dataset
uspto-grants-2014_02
Patent number
US08642776B2

Reaction notes

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