1,3-Dibromo-5,5-dimethylhydantoin → (4-Bromo-2-fluorophenyl)(2-(diethoxymethyl)phenyl)methanone

HRID 475425ノート

反応式

HRID 475425 の反応式
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[CH:16]([O:20][CH2:21][CH3:22])[O:17][CH2:18][CH3:19])[OH:9])=[C:4]([F:23])[CH:3]=1.C(=O)(O)[O-].[Na+].BrN1C(C)(C)C(=O)N(Br)C1=O.S([O-])([O-])(=O)=S.[Na+].[Na+]>C(O)(C)(C)C.CC1(C)N([O])C(C)(C)CCC1.O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[CH:16]([O:17][CH2:18][CH3:19])[O:20][CH2:21][CH3:22])=[O:9])=[C:4]([F:23])[CH:3]=1

参加物

8

反応物 4

HCID 64791,3-Dibromo-5,5-dimethylhydantoinHCID 24477Sodium ThiosulfateHCID 516892Sodium Bicarbonate2 回HCID 66847952(4-Bromo-2-fluorophenyl)(2-(diethoxymethyl)phenyl)methanol2 回

生成物 1

HCID 66848092(4-Bromo-2-fluorophenyl)(2-(diethoxymethyl)phenyl)methanone収率 102.3%

試薬・触媒・溶媒 3

HCID 2724126Tempo触媒HCID 962Water溶媒HCID 6386tert-Butanol溶媒

実験手順

(4-bromo-2-fluorophenyl)(2-(diethoxymethyl)phenyl)methanol (Compound 1a) (116 g) was dissolved in t-butanol (680 mL) with stirring and to the resulting solution was added water (1.4 ) followed by sodium bicarbonate (54.2 g). Using a water bath used to keep temperature around 20° C., 1,3-dibromo-5,5-dimethylhydantoin (48.3 g) and then TEMPO (0.51 g) was added and the cloudy yellow coloured suspension stirred at room temperature overnight. Saturated sodium bicarbonate (360 mL) and sodium thiosulfate (48 g in water) was added. The resulting mixture was stirred for 10 min then extracted with ethyl acetate, the extracts were washed with brine, dried over anhydrous sodium sulfate and evaporated to give the title product (118 g) as a dark yellow oil.

後処理

  1. stirringstirred at room temperature overnight
  2. stirringThe resulting mixture was stirred for 10 min
  3. extractionthen extracted with ethyl acetate
  4. washthe extracts were washed with brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. customevaporated

出典と根拠

ORDレコード
ord-be3cbe9ac47748adbb91f5d9b1527c46
出典データセット
uspto-grants-2014_01
特許番号
US08637551B2

反応ノート

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