1-Bromo-4-iodobenzene → 8-(4-Bromophenyl)-1,4-dioxa-8-azaspiro[4.5]decane

HRID 41700

Reaction equation

HRID 41700 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5](I)=[CH:4][CH:3]=1.[O:9]1[C:13]2([CH2:18][CH2:17][NH:16][CH2:15][CH2:14]2)[O:12][CH2:11][CH2:10]1.C1(P(C2C=CC=CC=2)C2C3OC4C(=CC=CC=4P(C4C=CC=CC=4)C4C=CC=CC=4)C(C)(C)C=3C=CC=2)C=CC=CC=1.CC(C)([O-])C.[Na+]>C1(C)C=CC=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C(OCC)(=O)C>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([N:16]2[CH2:17][CH2:18][C:13]3([O:12][CH2:11][CH2:10][O:9]3)[CH2:14][CH2:15]2)=[CH:4][CH:3]=1

Participants

8

Reactant 4

HCID 115221-Bromo-4-iodobenzeneHCID 674351,4-Dioxa-8-azaspiro(4.5)decaneHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 23676156Sodium t-butoxide

Product 1

HCID 121693418-(4-Bromophenyl)-1,4-dioxa-8-azaspiro[4.5]decaneYield 58.8%

Reagents, catalysts & solvents 3

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

0.5 g of 1-bromo-4-iodobenzene and 0.3 g of 1,4-dioxa-8-azaspiro[4.5]decane are placed in 10 ml of toluene and then 0.08 g of tris(dibenzylideneacetone)dipalladium(0), 0.061 g of 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene and 0.255 g of sodium tert-butoxide are added. The reaction medium is brought to reflux of the solvent for 4 h. Ethyl acetate is subsequently added and the mixture is washed twice with water and once with a saturated aqueous sodium chloride solution. The organic phase is dried over magnesium sulphate and concentrated under reduced pressure. The crude product obtained is chromatographed on silica gel, elution being carried out with a heptane/ethyl acetate (4/1) solvent mixture. 0.31 g of 8-(4-bromophenyl)-1,4-dioxa-8-azaspiro[4.5]decane is obtained.

Workup

  1. temperatureto reflux of the solvent for 4 h
  2. washthe mixture is washed twice with water and once with a saturated aqueous sodium chloride solution
  3. dry with materialThe organic phase is dried over magnesium sulphate
  4. concentrationconcentrated under reduced pressure
  5. customThe crude product obtained
  6. customis chromatographed on silica gel, elution

Sources & evidence

ORD record
ord-bfdb6ef5a9a9453989e933069f5009fe
Source dataset
uspto-grants-2013_09
Patent number
US08530657B2

Linked notes

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