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

HRID 41700

反応式

HRID 41700 の反応式
[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

参加物

8

反応物 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

生成物 1

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

試薬・触媒・溶媒 3

HCID 9811564Bis(dibenzylideneacetone)palladium触媒HCID 1140Toluene溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-bfdb6ef5a9a9453989e933069f5009fe
出典データセット
uspto-grants-2013_09
特許番号
US08530657B2

関連ノート

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