Chlorobenzene → methyl 7-chloronaphthalene-1-carboxylate

HRID 1876278Notes

Reaction equation

HRID 1876278 reaction equation
O1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]([O:8][CH3:9])=[O:7].[Cl:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.[Al+3].[Cl-].[Cl-].[Cl-]>CCOCC>[CH3:9][O:8][C:6]([C:2]1[C:15]2[C:14](=[CH:13][CH:12]=[C:11]([Cl:10])[CH:16]=2)[CH:5]=[CH:4][CH:3]=1)=[O:7]

Participants

5

Reactant 3

HCID 7964ChlorobenzeneHCID 11902Methyl 2-furoateHCID 6451240Aluminum(III) Chloride

Product 1

HCID 230778methyl 7-chloronaphthalene-1-carboxylate

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A mixture of 50 ml of methyl 2-furoate and 400 ml of chlorobenzene is stirred at 0° for 30 minutes, at RT for 1.5 hours and at 100° for 16 hours. 121 g of anhydrous AlCl3 are added by portion at 0°. The solution obtained is cooled, poured in an ice-bath and stirred for 30 minutes before extraction of the aq. phase with ether. The organic phase obtained is washed with aq. 10% NaHCO3 solution and brine, dried and solvent is evaporated. The residue obtained is purified by flash chromatography on silica gel (eluent: cyclohexane/EtOAc 99/1 to 95/5) to obtain the title compound.

Workup

  1. customThe solution obtained
  2. temperatureis cooled
  3. additionpoured in an ice-bath
  4. customThe organic phase obtained
  5. washis washed with aq. 10% NaHCO3 solution and brine
  6. customdried
  7. customsolvent is evaporated
  8. customThe residue obtained
  9. customis purified by flash chromatography on silica gel (eluent: cyclohexane/EtOAc 99/1 to 95/5)

Sources & evidence

ORD record
ord-eff43dfb1c7f47de92ea37f242254d91
Source dataset
uspto-grants-2012_11
Patent number
US08309596B2

Reaction notes

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