Water → 4′-(Dimethylamino)-4-hydroxy[1,1′-biphenyl]-3-carboxaldehyde

HRID 1686142Notes

Reaction equation

HRID 1686142 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]([OH:10])=[C:6]([CH:9]=1)[CH:7]=[O:8].[CH3:11][N:12]([CH3:22])[C:13]1[CH:18]=[CH:17][C:16](B(O)O)=[CH:15][CH:14]=1.C(=O)([O-])[O-].[Na+].[Na+].O>COCCOC.C(OCC)(=O)C.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.[Fe+2]>[CH3:11][N:12]([CH3:22])[C:13]1[CH:18]=[CH:17][C:16]([C:2]2[CH:3]=[CH:4][C:5]([OH:10])=[C:6]([CH:7]=[O:8])[CH:9]=2)=[CH:15][CH:14]=1

Participants

9

Reactant 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 728635-BromosalicylaldehydeHCID 27343444-(Dimethylamino)phenylboronic acid

Product 1

HCID 597846484′-(Dimethylamino)-4-hydroxy[1,1′-biphenyl]-3-carboxaldehydeYield 64%

Reagents, catalysts & solvents 4

HCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)Catalyst2×HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 80711,2-DimethoxyethaneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

Within a vacuum tube, 5-bromo-2-hydroxybenzaldehyde (0.5 g, 2.49 mmol), 4-dimethylaminophenyl boronic acid (0.62 g, 3.73 mg), dichloro[1,1′-ferrocenylbis(diphenyl-phosphine)]palladium(II)dichloromethane (Pd(dppf)Cl2, 0.33 g, 0.40 mmol, ‘dppf’=1,1′-bis(diphenylphospino)ferrocene) and sodium carbonate (0.53 g, 4.98 mmol) were dissolved in ethylene glycol dimethylether:water (15 ml:5 ml), followed by stirring at 100° C. for 4 hours. The reaction product thus obtained was diluted in ethyl acetate, washed with brine, dried over anhydrous MgSO4, and concentrated. The concentrate was purified through column chromatography (10% ethyl acetate/hexane) and the fraction was concentrated to give 4′-dimethylamino-4-hydroxybiphenyl-3-carbaldehyde (0.383 g, 64%).

Workup

  1. customThe reaction product thus obtained
  2. washwashed with brine
  3. dry with materialdried over anhydrous MgSO4
  4. concentrationconcentrated
  5. customThe concentrate was purified through column chromatography (10% ethyl acetate/hexane)
  6. concentrationthe fraction was concentrated

Sources & evidence

ORD record
ord-089e59e52a95447eba4bfa0a929b2741
Source dataset
uspto-grants-2012_04
Patent number
US08148541B2

Reaction notes

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