1,2-Dimethoxyethane → 4'-Chloro-3-hydroxybiphenyl-2-carbaldehyde

HRID 1043204

Reaction equation

HRID 1043204 reaction equation
Br[C:2]1[CH:9]=[CH:8][CH:7]=[C:6]([OH:10])[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(COC)OC.C([O-])([O-])=O.[Na+].[Na+]>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.O.C(O)C>[Cl:11][C:12]1[CH:17]=[CH:16][C:15]([C:2]2[C:3]([CH:4]=[O:5])=[C:6]([OH:10])[CH:7]=[CH:8][CH:9]=2)=[CH:14][CH:13]=1

Participants

9

Reactant 4

HCID 80711,2-DimethoxyethaneHCID 10340Sodium CarbonateHCID 742994-Chlorophenylboronic acidHCID 119547682-Bromo-6-hydroxybenzaldehyde

Product 1

HCID 866428814'-Chloro-3-hydroxybiphenyl-2-carbaldehyde

Reagents, catalysts & solvents 4

HCID 178418397HCID 178418397, compoundCatalystHCID 702EthanolSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
90 °C

Procedure

2-Bromo-6-hydroxybenzaldehyde (2.0 g), 4-chlorophenylboronic acid (1.86 g) and tetrakis(triphenylphosphine)palladium(0) (0.575 g) were suspended in a mixed solvent of dimethoxyethane (7 mL), ethanol (2 mL) and 2N Na2CO3 aqueous solution (5 mL). The reaction mixture was heated at 90° C. for 2 hours. The reaction mixture was diluted with ethyl acetate and poured into water. The organic layer was washed with water and with brine, dried over anhydrous sodium sulfate, filtered, and concentrated. The resulting solid was triturated with methanol and filtered to afford the title compound.

Workup

  1. washThe organic layer was washed with water and with brine
  2. dry with materialdried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe resulting solid was triturated with methanol
  6. filtrationfiltered

Sources & evidence

ORD record
ord-9249c183a6454a269ab02da63574bc48
Source dataset
uspto-grants-2013_10
Patent number
US08557983B2

Linked notes

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