Potassium Carbonate → 4'-Methoxy-(1,1'-biphenyl)-4-carboxaldehyde

HRID 922309Notes

Reaction equation

HRID 922309 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6](B(O)O)=[CH:5][CH:4]=1.Br[C:13]1[CH:20]=[CH:19][C:16]([CH:17]=[O:18])=[CH:15][CH:14]=1.C(=O)([O-])[O-].[K+].[K+]>O.C(O)C.O.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>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:13]2[CH:20]=[CH:19][C:16]([CH:17]=[O:18])=[CH:15][CH:14]=2)=[CH:5][CH:4]=1

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 707414-BromobenzaldehydeHCID 201262(4-Methoxyphenyl)boronic acid

Product 1

HCID 13944874'-Methoxy-(1,1'-biphenyl)-4-carboxaldehydeYield 71.4%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 19096565Water ethanolSolvent

Procedure

To a solution of (4-methoxyphenyl)boronic acid (1 g, 6.6 mmol) and 4-bromobenzaldehyde (1.2 g, 3.5 mmol) in ethanol water mixture was added potassium carbonate (1.7 g, 12.0 mmol) and degasified well and added tetrakis (0.7 g, 0.6 mmol) and stirred under argon for 12 h, reaction mass diluted with water and extracted with ethyl acetate, organic layer was washed with water and brine solutions, dried over anhydrous Na2SO4 and concentrated to brown solid as product (1 g, yield: 71.4%). 1H NMR (300 MHz, CDCl3): δ 9.96 (s, 1H), 7.84 (d, 2H), 7.63-7.66 (d, 2H), 7.51-7.54 (s, 2H), 6.93-6.95 (d, 2H), 3.80 (s, 3H)

Workup

  1. customreaction mass
  2. extractionextracted with ethyl acetate, organic layer
  3. washwas washed with water and brine solutions
  4. dry with materialdried over anhydrous Na2SO4
  5. concentrationconcentrated to brown solid as product (1 g, yield: 71.4%)

Sources & evidence

ORD record
ord-f6ce36ce66224d389e4ed3750ba11f94
Source dataset
uspto-grants-2016_03
Patent number
US09278915B2

Reaction notes

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