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

HRID 849559Notes

Reaction equation

HRID 849559 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 (4.50 mmol) 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, chromatographed 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
  10. customchromatographed on silica gel eluting with a gradient of hexane ethyl acetate=10:1 to 5:1

Sources & evidence

ORD record
ord-2c0465a2ac2449679005b20a2af1b602
Source dataset
uspto-grants-2000_01
Patent number
US06013652

Reaction notes

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