1,3-Dibromo-5,5-dimethylhydantoin → HCID 19915440, compound

HRID 1090494Notes

Reaction equation

HRID 1090494 reaction equation
[Cl:1][CH2:2][C:3]([C:13]1[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=1)([OH:12])[CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[Cl:11].[Br:20]N1C(C)(C)C(=O)N(Br)C1=O>ClC(Cl)(Cl)Cl>[Br:20][CH:4]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[Cl:11])[C:3]([C:13]1[CH:14]=[CH:15][C:16]([F:19])=[CH:17][CH:18]=1)([OH:12])[CH2:2][Cl:1]

Participants

4

Reactant 2

HCID 64791,3-Dibromo-5,5-dimethylhydantoinHCID 10935427HCID 10935427, compound

Product 1

HCID 19915440HCID 19915440, compound

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

4.0 g (13.4 mmol) of 1-chloro-3-(2-chlorophenyl)-2-(4-fluorophenyl)-2-propanol are photobrominated with 2.3 g (8.0 mmol) of 1,3-dibromo-5,5-dimethylhydantoin in 80 ml of tetrachloromethane at 35° C. while stirring vigorously and irradiating with mixed light from an Osram HWL 235 V/500 W lamp. The hydantoin is filtered off with suction, the filtrate is extracted with dilute sodium carbonate solution and water, and conventional working up provides 5.1 g of crude product as an oil which is employed for the next stage. The erythro:threo isomer ratio found from the signals for the --CHBr--groups in the 1H-NMR spectrum, which appear at 6.4 ppm for the erythro compounds and at 6.2 ppm for the threo compound (each measured in CDCl3), is 4:1. The erythro isomer is also characterized by a doublet of doublets at 4.1 ppm.

Workup

  1. customirradiating
  2. additionwith mixed light from an Osram HWL 235 V/500 W lamp
  3. filtrationThe hydantoin is filtered off with suction
  4. extractionthe filtrate is extracted with dilute sodium carbonate solution and water

Sources & evidence

ORD record
ord-55d529e26da9426fa9535975290f0b3c
Source dataset
uspto-grants-1992_01
Patent number
US05081317

Reaction notes

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