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

HRID 539850

Reaction equation

HRID 539850 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) 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, 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-ac0c4465c37549558f992d061d6115f1
Source dataset
uspto-grants-2014_10
Patent number
US08871775B2

Linked notes

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