Methyl 4-iodobenzoate → HCID 10619533, compound

HRID 2395407Notes

Reaction equation

HRID 2395407 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6](Br)=[CH:5][C:4]=1[O:10][CH2:11][CH2:12][CH2:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.[Li]CCCC.C[O:27][C:28](=[O:36])[C:29]1[CH:34]=[CH:33][C:32](I)=[CH:31][CH:30]=1>C1COCC1.CCOCC.[Cl-].[Cl-].[Zn+2].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[Pd]>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:32]2[CH:33]=[CH:34][C:29]([C:28]([OH:36])=[O:27])=[CH:30][CH:31]=2)=[CH:5][C:4]=1[O:10][CH2:11][CH2:12][CH2:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

8

Reactant 3

HCID 69273Methyl 4-iodobenzoateHCID 10806695HCID 10806695, compoundHCID 178418339Butyllithium

Product 1

HCID 10619533HCID 10619533, compound

Reagents, catalysts & solvents 4

HCID 3007855ZincchlorideCatalystHCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (2.9 g, 8.65 mmol, 1.0 eq) 1-methoxy-2-(4-phenyl-1-butoxy)-4-bromobenzene in 30 ml of dry THF at -78° C. was added (3.81 ml, 9.52 mmol, 1.1 eq) 2.5M n-BuLi. After stirring 15 minutes at -78° C. (10.4 ml, 10.4 mmol, 1.2 eq) 1.0M ZnCl2 in ether was added and the mixture allowed to warm to room temperature over 35 minutes. Tetrakis(triphenylphosphine)palladium(O) (500 mg, 0.43 mmol, 0.05 eq) and (2.27 g, 8.65 mmol, 1.0 eq) methyl-4-iodobenzoate were added to the reaction and the mixture allowed to stir at room temperature for 2.5 hours. The reaction mixture was concentrated in vacuo, costripped with CHCl3, and chromatographed on a silica gel column eluting with ethyl acetate-hexane (0-10%) to afford 2.61 g, 76%, of a yellow solid. Hydrolysis of the ester according to the method of Example 4 gave the title compound, M.P.: 178°-179° C. Elemental analysis calculated for C24H24O4 : C, 76.56; H, 6.43. Found: C, 76.06; H, 5.92.

Workup

  1. additionwas added
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. customchromatographed on a silica gel column
  4. washeluting with ethyl acetate-hexane (0-10%)
  5. customto afford 2.61 g, 76%

Sources & evidence

ORD record
ord-237c538315f141ba830233920bf505b1
Source dataset
uspto-grants-1998_09
Patent number
US05814651

Reaction notes

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