Water → Methyl 4-([1,1'-biphenyl]-3-ylmethoxy)benzenepropanoate

HRID 1678567Notes

Reaction equation

HRID 1678567 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH2:8][O:9][C:10]2[CH:15]=[CH:14][C:13]([CH2:16][CH2:17][C:18]([O:20][CH3:21])=[O:19])=[CH:12][CH:11]=2)[CH:5]=[CH:6][CH:7]=1.B([O-])O[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.C(=O)([O-])[O-].[Na+].[Na+].O>C1(C)C(CO)=CC=CC=1.O>[C:2]1([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH:7]=[CH:6][CH:5]=[C:4]([CH2:8][O:9][C:10]2[CH:15]=[CH:14][C:13]([CH2:16][CH2:17][C:18]([O:20][CH3:21])=[O:19])=[CH:12][CH:11]=2)[CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 23136270Methyl 4-[(3-bromophenyl)methoxy]benzenepropanoateHCID 178514829HCID 178514829, compound

Product 1

HCID 23082944Methyl 4-([1,1'-biphenyl]-3-ylmethoxy)benzenepropanoateYield 93.4%

Reagents, catalysts & solvents 1

HCID 66808090HCID 66808090, compoundSolvent

Procedure

Methyl 4-[(3-bromophenyl)methoxy]benzenepropanoate (0.60 g, 1.7 mmol), phenyl boronate (0.25 g, 2.1 mmol) and sodium carbonate (0.55 g, 5.2 mmol) were dissolved in toluene-methanol-water (5:1:1, 35 mL), the mixture was purged with argon, and then tetrakistriphenylphosphine palladium (99 mg, 0.086 mmol) was added thereto. The reaction solution was heated under reflux overnight under argon atmosphere. The reaction solution was cooled, and then water was added to the reaction solution, followed by extraction with ethyl acetate. The extract was washed with water, dried and then concentrated. The residue was purified with silica gel column chromatography (hexane/ethyl acetate=18:1) to give the title compound (0.55 g, yield 92%) as white powders.

Workup

  1. customthe mixture was purged with argon
  2. temperatureThe reaction solution was heated
  3. temperatureunder reflux overnight under argon atmosphere
  4. temperatureThe reaction solution was cooled
  5. extractionfollowed by extraction with ethyl acetate
  6. washThe extract was washed with water
  7. customdried
  8. concentrationconcentrated
  9. customThe residue was purified with silica gel column chromatography (hexane/ethyl acetate=18:1)

Sources & evidence

ORD record
ord-0b4f74c77ac3488fa3fa43aa98fc548c
Source dataset
uspto-grants-2011_08
Patent number
US08008525B2

Reaction notes

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