Bromobenzene → HCID 19601773, compound

HRID 610745Notes

Reaction equation

HRID 610745 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Li]CCCC.[C:13]([C:16]1[CH:17]=[C:18]([C:26](=[O:28])[CH3:27])[CH:19]=[C:20]([C:22]([CH3:25])([CH3:24])[CH3:23])[CH:21]=1)(=[O:15])[CH3:14]>C1COCC1>[C:22]([C:20]1[CH:21]=[C:16]([C:13](=[O:15])[CH3:14])[CH:17]=[C:18]([C:26]([OH:28])([C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH3:27])[CH:19]=1)([CH3:23])([CH3:25])[CH3:24]

Participants

5

Reactant 3

HCID 7961BromobenzeneHCID 19601772HCID 19601772, compoundHCID 178418339Butyllithium

Product 1

HCID 19601773HCID 19601773, compoundYield 77.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To 288.0 mg (1.83 mmol) of bromobenzene in 8 ml of dry THF at -78° C. was added 734 ml (1.83 mmol) of n-BuLi (2.5 M in hexanes). The reaction was stirred for 10 min followed by addition of 400 mg (1.83 mmol) of diketone 14 in 2 ml of dry THF. After stirring for 30 min, the mixture was quenched with saturated aqueous NH4Cl and the products were extracted with EtOAc. The EtOAc extracts were washed with water, brine, dried, filtered, and concentrated to give 420 mg of crude compound 15 which was used in the next step without further purification. TLC (20% EtOAC-80% hexanes) Rf 0.7.

Workup

  1. stirringAfter stirring for 30 min
  2. customthe mixture was quenched with saturated aqueous NH4Cl
  3. extractionthe products were extracted with EtOAc
  4. washThe EtOAc extracts were washed with water, brine
  5. customdried
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-e6863d0549204a81a504b6a6be2057b3
Source dataset
uspto-grants-1999_12
Patent number
US05998654

Reaction notes

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