Ethanol → HCID 86642871, compound

HRID 1043066Notes

Reaction equation

HRID 1043066 reaction equation
Br[C:2]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][C:3]=1[CH:4]=[O:5].[Cl:11][C:12]1[CH:17]=[CH:16][C:15](B(O)O)=[CH:14][CH:13]=1.C(O)C.C([O-])([O-])=O.[Na+].[Na+]>C(COC)OC.C(OCC)(=O)C>[Cl:11][C:12]1[CH:17]=[CH:16][C:15]([C:2]2[C:3]([CH:4]=[O:5])=[CH:6][C:7]([OH:10])=[CH:8][CH:9]=2)=[CH:14][CH:13]=1

Participants

7

Reactant 4

HCID 702EthanolHCID 10340Sodium CarbonateHCID 742994-Chlorophenylboronic acidHCID 3871792-Bromo-5-hydroxybenzaldehyde

Product 1

HCID 86642871HCID 86642871, compound

Reagents, catalysts & solvents 2

HCID 80711,2-DimethoxyethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

2-bromo-5-hydroxybenzaldehyde (20 g), 4-chlorophenylboronic acid (17.1 g) and dichlorobis(triphenylphosphine) palladium(II) (1.75 g) were dissolved in 475 mL of a dimethoxyethane:ethanol:2M Na2CO3 solution (7:2:2). The mixture was heated to reflux for 1 hour. The reaction mixture was then diluted with ethyl acetate, washed thoroughly with water and with brine, dried over MgSO4, filtered and concentrated. The resulting solid was slurried in 500 mL of hexane:ether mixture (2:1). The title compound was collected by filtration.

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 1 hour
  3. washwashed thoroughly with water and with brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. filtrationThe title compound was collected by filtration

Sources & evidence

ORD record
ord-828dc63ceb034fd8ab441edd633f673d
Source dataset
uspto-grants-2013_10
Patent number
US08557983B2

Reaction notes

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