Water → HCID 1393824, compound

HRID 969473Notes

Reaction equation

HRID 969473 reaction equation
C(=O)([O-])[O-].[K+].[K+].I[C:8]1[CH:13]=[CH:12][C:11]([Br:14])=[CH:10][CH:9]=1.[CH:15]([C:17]1[CH:18]=[C:19](B(O)O)[CH:20]=[CH:21][CH:22]=1)=[O:16].O>C1(C)C=CC=CC=1.C1(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)C=CC=CC=1>[Br:14][C:11]1[CH:12]=[CH:13][C:8]([C:21]2[CH:20]=[CH:19][CH:18]=[C:17]([CH:15]=[O:16])[CH:22]=2)=[CH:9][CH:10]=1

Participants

7

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 115221-Bromo-4-iodobenzeneHCID 27343563-Formylphenylboronic acid

Product 1

HCID 1393824HCID 1393824, compoundYield 33.2%

Reagents, catalysts & solvents 2

HCID 178420554HCID 178420554, compoundCatalystHCID 1140TolueneSolvent

Procedure

89 ml (180 mmol) of a 2M solution of potassium carbonate are added to a solution containing 20 g (71 mmol) of p-iodobromobenzene and 14 g (92 mmol) of 3-formylbenzeneboronic acid in toluene, followed by addition of 4.1 g (3.5 mmol) of tetrakis(triphenylphosphino)palladium. The reaction medium is refluxed for 16 hours. After cooling to room temperature, water is added and the organic products are extracted with ethyl acetate. The solvents are evaporated off and the residue obtained is purified by chromatography on silica with a 99/1 heptane/ethyl acetate mixture. 6.2 g (23.6 mmol) of the expected aldehyde, an orange solid, are isolated in a yield of 33%.

Workup

  1. temperatureThe reaction medium is refluxed for 16 hours
  2. extractionthe organic products are extracted with ethyl acetate
  3. customThe solvents are evaporated off
  4. customthe residue obtained
  5. customis purified by chromatography on silica with a 99/1 heptane/ethyl acetate mixture

Sources & evidence

ORD record
ord-c9688cefc84e4d289ee74f600db79f7d
Source dataset
uspto-grants-2007_12
Patent number
US07307078B2

Reaction notes

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