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

HRID 475425Notes

Reaction equation

HRID 475425 reaction equation
[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

Participants

8

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 3

HCID 2724126TempoCatalystHCID 962WaterSolventHCID 6386tert-ButanolSolvent

Procedure

(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.

Workup

  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

Sources & evidence

ORD record
ord-be3cbe9ac47748adbb91f5d9b1527c46
Source dataset
uspto-grants-2014_01
Patent number
US08637551B2

Reaction notes

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