Potassium Carbonate → 1-(Chloromethyl)-2-fluoro-3-methoxybenzene

HRID 1443144Notes

Reaction equation

HRID 1443144 reaction equation
[F:1][C:2]1[C:9]([O:10][CH3:11])=[CH:8][CH:7]=[CH:6][C:3]=1[CH2:4]O.S(Cl)([Cl:14])=O.C(=O)([O-])[O-].[K+].[K+]>ClCCl.C(OC)(C)(C)C>[F:1][C:2]1[C:9]([O:10][CH3:11])=[CH:8][CH:7]=[CH:6][C:3]=1[CH2:4][Cl:14]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 24386Thionyl ChlorideHCID 5935892-Fluoro-3-methoxybenzyl alcohol

Product 1

HCID 538708331-(Chloromethyl)-2-fluoro-3-methoxybenzene

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 15413tert-Butyl methyl etherSolvent

Procedure

24.79 g (158.75 mmol) of 2-fluoro-3-methoxybenzyl alcohol is dissolved in 35 ml of dichloromethane. While being cooled slightly, 58.4 ml of thionyl chloride is added in drops, and the batch is then stirred overnight at room temperature. The reaction mixture is spun in until a dry state is reached, the residue is dissolved in methyl tert-butyl ether, and it is shaken twice with semi-saturated potassium carbonate solution. The aqueous phase is extracted once with methyl tert-butyl ether. The combined organic extracts are worked up as usual. The residue that is obtained is incorporated in crude form into the next stage.

Workup

  1. temperatureWhile being cooled slightly
  2. extractionThe aqueous phase is extracted once with methyl tert-butyl ether
  3. customThe residue that is obtained

Sources & evidence

ORD record
ord-a9a6b7605c444130a32f61aeeae913c6
Source dataset
uspto-grants-2010_02
Patent number
US07659297B2

Reaction notes

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