Boron Trichloride → Methyl (2-chloro-4'-hydroxy-1,1'-biphenyl-4-yl)acetate

HRID 2076624Notes

Reaction equation

HRID 2076624 reaction equation
B(Cl)(Cl)Cl.[Cl:5][C:6]1[CH:11]=[C:10]([CH2:12][C:13]([O:15][CH3:16])=[O:14])[CH:9]=[CH:8][C:7]=1[C:17]1[CH:22]=[CH:21][C:20]([O:23]C)=[CH:19][CH:18]=1>[I-].C([N+](CCCC)(CCCC)CCCC)CCC.C(Cl)Cl>[Cl:5][C:6]1[CH:11]=[C:10]([CH2:12][C:13]([O:15][CH3:16])=[O:14])[CH:9]=[CH:8][C:7]=1[C:17]1[CH:22]=[CH:21][C:20]([OH:23])=[CH:19][CH:18]=1

Participants

5

Reactant 2

HCID 25135Boron TrichlorideHCID 86088062Methyl (2-chloro-4'-methoxy-1,1'-biphenyl-4-yl)acetate

Product 1

HCID 86088067Methyl (2-chloro-4'-hydroxy-1,1'-biphenyl-4-yl)acetateYield 71.3%

Reagents, catalysts & solvents 2

HCID 67553Tetrabutylammonium IodideCatalystHCID 6344DichloromethaneSolvent

Procedure

After boron trichloride (1.0N methylene chloride solution, 1.8 ml, 1.8 mmol) was added to a solution of methyl (2-chloro-4′-methoxy-1,1′-biphenyl-4-yl)acetate (228 mg, 0.73 mmol) obtained in Example (23-2) and tetra-n-butylammonium iodide (325 mg, 0.88 mmol) in methylene chloride (4 ml) at −78° C., the temperature of the mixture was raised to room temperature and the mixture was stirred for 2 hours. Ice was added to the reaction mixture and the mixture was extracted with ethyl acetate. The organic layer was successively washed with water and a saturated aqueous NaCl solution and dried with anhydrous sodium sulfate. The residue obtained by removing the solvent under reduced pressure was purified by silica gel column chromatography (eluting solvent: n-hexane/ethyl acetate=10/1-2/1) to give methyl (2-chloro-4′-hydroxy-1,1′-biphenyl-4-yl)acetate as a colorless solid (144 mg, yield: 71%).

Workup

  1. additionIce was added to the reaction mixture
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe organic layer was successively washed with water
  4. dry with materiala saturated aqueous NaCl solution and dried with anhydrous sodium sulfate
  5. customThe residue obtained
  6. customby removing the solvent under reduced pressure
  7. customwas purified by silica gel column chromatography (eluting solvent: n-hexane/ethyl acetate=10/1-2/1)

Sources & evidence

ORD record
ord-12baa08b0d53425aa02742d66c9a5659
Source dataset
uspto-grants-2011_04
Patent number
US07923573B2

Reaction notes

Loading…