Benzene, 1-bromo-3,5-dimethyl- → HCID 18392763, compound

HRID 1737442Notes

Reaction equation

HRID 1737442 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C@@H:9]([CH2:30][CH2:31][C:32]([C:34]2[CH:39]=[C:38]([CH3:40])[CH:37]=[C:36]([CH3:41])[CH:35]=2)=[O:33])CCN2CCC3(C4C(=CC=CC=4)N(S(C)(=O)=O)C3)CC2)[CH:5]=[CH:6][C:7]=1[Cl:8].[CH3:42][C:43]1C=C([Mg]Br)C=C(C)[CH:48]=1.BrC1C=C(C)C=C(C)C=1.[Mg]>C1COCC1>[Cl:1][C:2]1[CH:3]=[C:4]([C@H:9]([CH2:48][CH:43]=[CH2:42])[CH2:30][CH2:31][C:32]([C:34]2[CH:39]=[C:38]([CH3:40])[CH:37]=[C:36]([CH3:41])[CH:35]=2)=[O:33])[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

6

Reactant 4

HCID 136357Benzene, 1-bromo-3,5-dimethyl-HCID 5462224MagnesiumHCID 18392699HCID 18392699, compoundHCID 178425074HCID 178425074, compound

Product 1

HCID 18392763HCID 18392763, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

1.42 g (4.50mmol) of (N-Methoxy-N-methyl)-(4-(S)-(3,4-dichlorophenyl)-6-heptenyl)-amide (prepared in Example 134) was dissolved in 20 mL of dry THF. To it added 10 mL THF solution of 3,5-dimethylphenylmagnesium bromide prepared from 1.8 g (9.6 mmol) of 5-bromo-m-xylene and 463 mg of magnesium turnings. After stirring for 2 hr at rt, the reaction was quenched with saturated aqueous ammonium chloride solution. THF was removed under reduced pressure. The residual material was diluted with ethyl acetate. The organic phase was separated, aqueous phase was extracted twice with ethyl acetate. Combined organic phases were washed with brine, dried over anhydrous magnesium sulfate, filtered, concentrated, chromatogrpraphed on silica gel eluting with a gradient of hexane ethyl acetate=10:1 to 5:1 to give 1.57 g of 4-(S)-(3,4-dichlorophenyl)-1-(3,5-dimethylphenyl)-hept-6-ene-1-one (97%).

Workup

  1. customthe reaction was quenched with saturated aqueous ammonium chloride solution
  2. customTHF was removed under reduced pressure
  3. additionThe residual material was diluted with ethyl acetate
  4. customThe organic phase was separated
  5. extractionaqueous phase was extracted twice with ethyl acetate
  6. washCombined organic phases were washed with brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-33c272cca0774834b8683d64f67216fd
Source dataset
uspto-grants-1999_10
Patent number
US05962462

Reaction notes

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