Sodium Carbonate → 4'-Chloro[1,1'-biphenyl]-4-carbaldehyde

HRID 2374748Notes

Reaction equation

HRID 2374748 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5](B(O)O)=[CH:4][CH:3]=1.Br[C:12]1[CH:19]=[CH:18][C:15]([CH:16]=[O:17])=[CH:14][CH:13]=1.C(=O)([O-])[O-].[Na+].[Na+]>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C(COC)OC>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:12]2[CH:19]=[CH:18][C:15]([CH:16]=[O:17])=[CH:14][CH:13]=2)=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 707414-BromobenzaldehydeHCID 742994-Chlorophenylboronic acid

Product 1

HCID 5925704'-Chloro[1,1'-biphenyl]-4-carbaldehydeYield 94%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 80711,2-DimethoxyethaneSolvent

Procedure

A mixture of 4-chlorobenzeneboronic acid (19.4 g, 1 equiv), 4-bromobenzaldehyde (22.9 g, 1 equiv), palladium(II) acetate (1.4 g, 0.05 equiv), aqueous sodium carbonate (30.3 g in 144 ml solution, 2 equiv) and dimethoxyethane (500 ml) was stirred at reflux under argon for 2.5 h, then evaporated to low volume and diluted with dichloromethane. Workup continued as in (a) above to give identical material (25.2 g, 94%). 1H-NMR (CDCl3) δ 10.05 (1H, s), 7.96 (2H, d), 7.73 (2H, d), 7.57 (2H, d), 7.46 (2H, d); MS (AP+) found (M+1)=217, C13H9ClO requires 216.

Workup

  1. temperatureat reflux under argon for 2.5 h
  2. customevaporated to low volume
  3. additiondiluted with dichloromethane

Sources & evidence

ORD record
ord-397a84e24bf2419baeebddea43eabfee
Source dataset
uspto-grants-2008_12
Patent number
US07462620B2

Reaction notes

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