Dichloromethane → HCID 68005838, compound

HRID 1026594Notes

Reaction equation

HRID 1026594 reaction equation
ClCCl.[F:4][C:5]1[CH:6]=[C:7]([C:15]2[CH:20]=[CH:19][C:18]([CH3:21])=[CH:17][C:16]=2[O:22]C)[CH:8]=[CH:9][C:10]=1[C:11]([O:13][CH3:14])=[O:12].B(Br)(Br)Br>O>[F:4][C:5]1[CH:6]=[C:7]([C:15]2[CH:20]=[CH:19][C:18]([CH3:21])=[CH:17][C:16]=2[OH:22])[CH:8]=[CH:9][C:10]=1[C:11]([O:13][CH3:14])=[O:12]

Participants

5

Reactant 3

HCID 6344Dichloromethane2×HCID 25134Boron tribromideHCID 68006210HCID 68006210, compound

Product 1

HCID 68005838HCID 68005838, compoundYield 15.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Under ice cooling, to a dichloromethane solution (10.0 ml) of methyl 3-fluoro-2′-methoxy-4′-methylbiphenyl-4-carboxylate (910 mg) was added a dichloromethane solution (1 M, 9.95 ml) of boron tribromide, followed by stirring at room temperature overnight. The reaction solution was poured into water, and extracted with dichloromethane. The organic layer was dried over anhydrous sodium sulfate, and concentrated under reduced pressure. To the resulting residue were added methanol (30.0 ml) and ethyl acetate (3.0 ml). Under ice cooling, a hexane solution (2 M, 8.30 ml) of trimethylsilyldiazomethane was added dropwise, and stirred at room temperature overnight. The reaction solution was concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography to afford methyl 3-fluoro-2′-hydroxy-4′-methylbiphenyl-4-carboxylate (137 mg).

Workup

  1. extractionextracted with dichloromethane
  2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  3. concentrationconcentrated under reduced pressure
  4. additionTo the resulting residue were added methanol (30.0 ml) and ethyl acetate (3.0 ml)
  5. additionUnder ice cooling, a hexane solution (2 M, 8.30 ml) of trimethylsilyldiazomethane was added dropwise
  6. stirringstirred at room temperature overnight
  7. concentrationThe reaction solution was concentrated under reduced pressure
  8. customthe resulting residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-a391615c48ed497686e9d3a6841d8b27
Source dataset
uspto-grants-2014_05
Patent number
US08729095B2

Reaction notes

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