Cesium fluoride → Methyl 3-(3-(((2'-(butyloxy)-2-methyl-5'-(methyloxy)-1,1'-biphenyl-4-yl)methyl)oxy)phenyl)propanoate

HRID 1662316Notes

Reaction equation

HRID 1662316 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([CH2:8][O:9][C:10]2[CH:11]=[C:12]([CH2:16][CH2:17][C:18]([O:20][CH3:21])=[O:19])[CH:13]=[CH:14][CH:15]=2)=[CH:4][C:3]=1[CH3:22].[F-].[Cs+].[CH2:25]([O:29][C:30]1[CH:35]=[CH:34][C:33]([O:36][CH3:37])=[CH:32][C:31]=1B(O)O)[CH2:26][CH2:27][CH3:28]>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.COCCOC>[CH2:25]([O:29][C:30]1[CH:31]=[CH:32][C:33]([O:36][CH3:37])=[CH:34][C:35]=1[C:2]1[CH:7]=[CH:6][C:5]([CH2:8][O:9][C:10]2[CH:11]=[C:12]([CH2:16][CH2:17][C:18]([O:20][CH3:21])=[O:19])[CH:13]=[CH:14][CH:15]=2)=[CH:4][C:3]=1[CH3:22])[CH2:26][CH2:27][CH3:28]

Participants

6

Reactant 3

HCID 25953Cesium fluorideHCID 57705717HCID 57705717, compoundHCID 57705740Methyl 3-(3-(((4-bromo-3-methylphenyl)methyl)oxy)phenyl)propanoate

Product 1

HCID 57707120Methyl 3-(3-(((2'-(butyloxy)-2-methyl-5'-(methyloxy)-1,1'-biphenyl-4-yl)methyl)oxy)phenyl)propanoateYield 95%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
85 °C

Procedure

To a 2 dram vial charged with 1.3 (0.0200 g, 0.0551 mmol), tetrakis(triphenylphosphine)palladium (0) (0.0127 g, 0.0110 mmol), cesium fluoride (0.0102 mL, 0.275 mmol), and 2-butoxy-5-methoxyphenylboronic acid 4.2 (0.0247 g, 0.110 mmol), was added DME (1 mL). The resulting mixture was then heated at 85° C. overnight. The reaction was allowed to cool and then filtered and concentrated. The crude was purified by combiflash (0 to 20% EtOAc/hexanes) yielding 4.3 (0.0241 g, 95% yield).

Workup

  1. temperatureto cool
  2. filtrationfiltered
  3. concentrationconcentrated
  4. customThe crude was purified by combiflash (0 to 20% EtOAc/hexanes)

Sources & evidence

ORD record
ord-387de3f967314ec1bd532930eda51fc8
Source dataset
uspto-grants-2011_10
Patent number
US08030354B2

Reaction notes

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