Methyl 4-iodobenzoate → HCID 20150449, compound

HRID 568350

Reaction equation

HRID 568350 reaction equation
C([Li])(C)(C)C.Br[C:7]1[CH:8]=[C:9]2[C:14](=[CH:15][CH:16]=1)[N:13]=[C:12]([O:17][CH3:18])[CH:11]=[CH:10]2.I[C:20]1[CH:29]=[CH:28][C:23]([C:24]([O:26][CH3:27])=[O:25])=[CH:22][CH:21]=1>CCCCC.O1CCCC1.[Cl-].[Zn+2].[Cl-].C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:18][O:17][C:12]1[CH:11]=[CH:10][C:9]2[C:14](=[CH:15][CH:16]=[C:7]([C:20]3[CH:29]=[CH:28][C:23]([C:24]([O:26][CH3:27])=[O:25])=[CH:22][CH:21]=3)[CH:8]=2)[N:13]=1

Participants

8

Reactant 3

HCID 69273Methyl 4-iodobenzoateHCID 106575386-Bromo-2-methoxyquinolineHCID 178418306HCID 178418306, compound

Product 1

HCID 20150449HCID 20150449, compound

Reagents, catalysts & solvents 4

HCID 3007855ZincchlorideCatalystHCID 178418397HCID 178418397, compoundCatalystHCID 8003PentaneSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

t-Butyllithium (30 cm3 of a 2.0M solution in n-pentane) was added dropwise at -70° to a stirred solution of 6-bromo-2-methoxyquinoline (7.14 g) in tetrahydrofuran (THF) (50 cm3) under nitrogen. After 10 minutes a solution of anhydrous zinc chloride (4.09 g) in THF (30 cm3) was added and the solution was allowed to warm to room temperature. A mixture of methyl 4-iodobenzoate (7.8 g) and tetrakis(triphenylphosphine)palladium (0) (0.32 g) was added and the mixture was heated under reflux for 1 hour. Volatile material was removed in vacuo and the residue was partitioned between chloroform (150 cm3) and a solution of ethylenediaminetetraacetic acid disodium salt (22.4 g) in water (400 cm3). The aqueous phase was further extracted with chloroform (2×100 cm3), and the combined and dried (MgSO4) organic extracts were evaporated to give a solid which was recrystallised from acetone to afford the title compound, m.p. 158°-161°, (6.81 g).

Workup

  1. additionwas added
  2. temperaturethe mixture was heated
  3. temperatureunder reflux for 1 hour
  4. customVolatile material was removed in vacuo
  5. customthe residue was partitioned between chloroform (150 cm3)
  6. extractionThe aqueous phase was further extracted with chloroform (2×100 cm3)
  7. dry with materialdried (MgSO4) organic extracts
  8. customwere evaporated
  9. customto give a solid which
  10. customwas recrystallised from acetone

Sources & evidence

ORD record
ord-c873097ab0774f12bf48fddca6ce579f
Source dataset
uspto-grants-1988_03
Patent number
US04728654

Linked notes

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