Ethyl Bromide → HCID 20239880, compound

HRID 364774Notes

Reaction equation

HRID 364774 reaction equation
[Mg].[CH2:2](Br)[CH3:3].[Cl:5][C:6]1[CH:7]=[C:8]([CH:25]=[CH:26][CH:27]=1)[C:9]([C:11]1[CH:16]=[CH:15][C:14]([O:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[CH:13][CH:12]=1)=[O:10].[Cl-].[NH4+]>O1CCCC1.CCOCC>[Cl:5][C:6]1[CH:7]=[C:8]([C:9]([C:11]2[CH:12]=[CH:13][C:14]([O:17][CH2:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)=[CH:15][CH:16]=2)([OH:10])[CH2:2][CH3:3])[CH:25]=[CH:26][CH:27]=1

Participants

7

Reactant 4

HCID 6332Ethyl BromideHCID 25517Ammonium ChlorideHCID 5462224MagnesiumHCID 20239876HCID 20239876, compound

Product 1

HCID 20239880HCID 20239880, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a Grignard reactant prepared from 7.2 g. of magnesium turnings and 32.6 g. of ethyl bromide in 120 ml. of dry ether a solution of 24 g. of 3-chloro-4'-benzyloxy-benzophenone in 120 ml. of tetrahydrofurane is added dropwise, with stirring at 0° to 5° C. The reaction mixture is then slightly boiled for 30 minutes, and the Grignard complex is decomposed with a saturated aqueous solution of ammonium chloride under cooling. The aqueous phase is extracted with ether, the combined organic phases are washed with saturated aqueous sodium chloride solution. After drying over anhydrous sodium sulfate, the solvent is distilled off under reduced pressure. Crystallization of the residue from a mixture of ethyl acetate and n-hexane yields 16.2 g. of the named compound, melting at 52°-53° C.

Workup

  1. temperatureunder cooling
  2. extractionThe aqueous phase is extracted with ether
  3. washthe combined organic phases are washed with saturated aqueous sodium chloride solution
  4. dry with materialAfter drying over anhydrous sodium sulfate
  5. distillationthe solvent is distilled off under reduced pressure
  6. customCrystallization of the residue
  7. additionfrom a mixture of ethyl acetate and n-hexane
  8. customyields 16.2 g

Sources & evidence

ORD record
ord-32ecc043c2ae43bf9df3eba5da995f7e
Source dataset
uspto-grants-1986_08
Patent number
US04605785

Reaction notes

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