4-Methoxybiphenyl → HCID 10928704, compound

HRID 1596056Notes

Reaction equation

HRID 1596056 reaction equation
[CH2:1]([O:4][C:5]([C:7]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH:10]=[CH:9][C:8]=1[CH2:17][CH2:18][CH2:19][C:20](O)=[O:21])=[O:6])[CH:2]=[CH2:3].S(Cl)(Cl)=O.[CH3:27][O:28][C:29]1[CH:34]=[CH:33][C:32]([C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)=[CH:31][CH:30]=1.[Cl-].[Al+3].[Cl-].[Cl-]>C1C=CC=CC=1.CN(C=O)C>[CH3:27][O:28][C:29]1[CH:34]=[CH:33][C:32]([C:35]2[CH:36]=[CH:37][C:38]([C:20](=[O:21])[CH2:19][CH2:18][CH2:17][C:8]3[CH:9]=[CH:10][C:11]4[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=4)[C:7]=3[C:5]([O:4][CH2:1][CH:2]=[CH2:3])=[O:6])=[CH:39][CH:40]=2)=[CH:31][CH:30]=1

Participants

7

Reactant 4

HCID 119434-MethoxybiphenylHCID 24386Thionyl ChlorideHCID 6451240Aluminum(III) ChlorideHCID 11833431HCID 11833431, compound

Product 1

HCID 10928704HCID 10928704, compoundYield 45.5%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 241BenzeneSolvent

Procedure

A solution of Example 11E (282 mg, 0.946 mmol) in benzene (5 mL) was treated with thionyl chloride (0.138 mL, 1.89 mmol) and DMF (1 drop), stirred at room temperature for 30 minutes, concentrated to dryness and redissolved in dichloromethane (5 mL). The resulting solution was treated with 4-methoxybiphenyl (348 mg, 1.89 mmol) and aluminum chloride (377 mg, 2.84 mmol) at 0° C., stirred at room temperature for 40 minutes, quenched with ice-water, extracted with dichloromethane, dried (Na2SO4), filtered, concentrated and purified on silica gel with a gradient of 5% to 20% ethyl acetate/hexanes to provide 200 mg (45%) of the desired compound contaminated with 30% of the ortho substituted isomer.

Workup

  1. concentrationconcentrated to dryness
  2. dissolutionredissolved in dichloromethane (5 mL)
  3. stirringstirred at room temperature for 40 minutes
  4. customquenched with ice-water
  5. extractionextracted with dichloromethane
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated
  9. custompurified on silica gel with a gradient of 5% to 20% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-c1f9399c2d484aaea1abc71a8ad82a21
Source dataset
uspto-grants-2001_09
Patent number
US06288261B1

Reaction notes

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