Iodine → HCID 14579587, compound

HRID 2184147Notes

Reaction equation

HRID 2184147 reaction equation
[Mg].[F:2][C:3]1[CH:4]=[C:5](Br)[CH:6]=[C:7]([F:9])[CH:8]=1.II.C([O:15][CH2:16][CH3:17])=O>CCOCC>[F:2][C:3]1[CH:4]=[C:5]([CH:16]([C:17]2[CH:4]=[C:3]([F:2])[CH:8]=[C:7]([F:9])[CH:6]=2)[OH:15])[CH:6]=[C:7]([F:9])[CH:8]=1

Participants

6

Reactant 4

HCID 807IodineHCID 8025Ethyl formateHCID 1363131-Bromo-3,5-difluorobenzene2×HCID 5462224Magnesium

Product 1

HCID 14579587HCID 14579587, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

A mixture of 486 mg magnesium, 8 mL dry ether, a small amount of 3,5-difluoro-bromobenzene and some iodine was warmed to start the Grignard reaction. 2.38 mL 3,5-difluoro-bromobenzene in 40 mL dry ether were added dropwise and the mixture refluxed for one hour. 0.81 mL ethyl formate was added and the mixture stirred for 21 hours at room temperature. The reaction was quenched with 7 mL 1N hydrochloric acid, diluted with ethyl acetate and washed with water and brine. Evaporation of the solvents and chromatography of the residue afforded 1.56 g of a light yellow solid, m.p.: 62° C.; MS: 315 ([M+AcO]−).

Workup

  1. customthe Grignard reaction
  2. temperaturethe mixture refluxed for one hour
  3. customThe reaction was quenched with 7 mL 1N hydrochloric acid
  4. additiondiluted with ethyl acetate
  5. washwashed with water and brine
  6. customEvaporation of the solvents and chromatography of the residue

Sources & evidence

ORD record
ord-89fc9cbb208746869de5fab904655021
Source dataset
uspto-grants-2005_05
Patent number
US06900227B2

Reaction notes

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