Sodium Carbonate → HCID 18922465, compound

HRID 1290011Notes

Reaction equation

HRID 1290011 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]([O:10][CH:11]([CH3:13])[CH3:12])=[C:6]([CH:9]=1)[CH:7]=[O:8].C(=O)([O-])[O-].[Na+].[Na+].[F:20][C:21]1[CH:26]=[CH:25][C:24](B(O)O)=[CH:23][CH:22]=1>COCCOC.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>[CH:11]([O:10][C:5]1[CH:4]=[CH:3][C:2]([C:24]2[CH:25]=[CH:26][C:21]([F:20])=[CH:22][CH:23]=2)=[CH:9][C:6]=1[CH:7]=[O:8])([CH3:13])[CH3:12]

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 2856454-Fluorophenylboronic acidHCID 8199735-Bromo-2-isopropoxybenzaldehyde

Product 1

HCID 18922465HCID 18922465, compound

Reagents, catalysts & solvents 3

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

Procedure

To a solution of 5-bromo-2-isopropoxy-benzaldehyde (504 mg, 2.07 mmol) in 1,2-dimethoxyethane (5 mL) were added tetrakis(triphenylphosphine)palladium(0) (87 mg, 0.075 mmol), 2M aqueous sodium carbonate (2.5 mL), and 4-fluorobenzeneboronic acid (396 mg, 2.83 mmol). The reaction mixture was stirred for 2 hours at reflux temperature, cooled, diluted with ethyl acetate, washed with water, saturated brine solution, dried (Na2SO4), and evaporated. The title compound was purified by flash chromatography eluting with 4% diethyl ether in hexane; yield 347 mg.

Workup

  1. temperatureat reflux temperature
  2. temperaturecooled
  3. washwashed with water, saturated brine solution
  4. dry with materialdried (Na2SO4)
  5. customevaporated
  6. customThe title compound was purified by flash chromatography
  7. washeluting with 4% diethyl ether in hexane

Sources & evidence

ORD record
ord-74674bc197844139a6988e2968eb06aa
Source dataset
uspto-grants-1998_05
Patent number
US05750549

Reaction notes

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