Potassium Carbonate → Methyl 2-(4'-methoxybiphenyl-4-yl)-2-phenylacetate

HRID 509195Notes

Reaction equation

HRID 509195 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:9]([O:11][CH3:12])=[O:10])=[CH:4][CH:3]=1.[CH3:19][O:20][C:21]1[CH:26]=[CH:25][C:24](B(O)O)=[CH:23][CH:22]=1.C(=O)([O-])[O-].[K+].[K+]>COCCOC.O.C(OCC)(=O)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:19][O:20][C:21]1[CH:26]=[CH:25][C:24]([C:2]2[CH:7]=[CH:6][C:5]([CH:8]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[C:9]([O:11][CH3:12])=[O:10])=[CH:4][CH:3]=2)=[CH:23][CH:22]=1

Participants

8

Reactant 3

HCID 11430Potassium CarbonateHCID 201262(4-Methoxyphenyl)boronic acidHCID 57779541Methyl 2-(4-bromophenyl)-2-phenylacetate

Product 1

HCID 57779556Methyl 2-(4'-methoxybiphenyl-4-yl)-2-phenylacetateYield 31%

Reagents, catalysts & solvents 4

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

To a degassed solution of bromide 54 (0.33 g, 1.081 mmol), 4-methoxyphenylboronic acid (0.181 g, 1.190 mmol), POT (0.023 g, 0.076 mmol) and potassium carbonate (0.747 g, 5.41 mmol) in DME (15 mL) and water (7.5 mL) was added Pd(PPh3)4 (0.087 g, 0.076 mmol). The reaction mixture was stirred at 80° C. for 16 h and diluted with ethyl acetate, washed with water, dried over Na2SO4, filtered and concentrated to afford compound 55 (0.11 g, 31% yield) as a white solid after purification by ISCO (2 to 40% EtOAc/hexane).

Workup

  1. washwashed with water
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-e2be10decd65499dbaa295ca5f3ac0cd
Source dataset
uspto-grants-2015_08
Patent number
US09096565B2

Reaction notes

Loading…