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

HRID 475425노트

반응식

HRID 475425 반응식
[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

참가 물질

8

반응물 4

HCID 64791,3-Dibromo-5,5-dimethylhydantoinHCID 24477Sodium ThiosulfateHCID 516892Sodium Bicarbonate2회HCID 66847952(4-Bromo-2-fluorophenyl)(2-(diethoxymethyl)phenyl)methanol2회

생성물 1

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

시약·촉매·용매 3

HCID 2724126Tempo촉매HCID 962Water용매HCID 6386tert-Butanol용매

실험 절차

(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.

후처리

  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

출처 및 근거

ORD 기록
ord-be3cbe9ac47748adbb91f5d9b1527c46
출처 데이터셋
uspto-grants-2014_01
특허 번호
US08637551B2

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