4-Bromobenzaldehyde → 4'-Chloro[1,1'-biphenyl]-4-carbaldehyde

HRID 967023Notes

Reaction equation

HRID 967023 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)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

5

Reactant 2

HCID 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) δ10.05 (1H, s), 7.96 (2H, d), 7.73 (2H,d), 7.57 (2H, d), 7.46 (2H, d); MS (AP+) found (M+1)=217, C13H935ClO 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-c7df0763b01041abb54f66785aa0b8fb
Source dataset
uspto-grants-2005_10
Patent number
US06953803B1

Reaction notes

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