Hydrochloric Acid → HCID 71212557, compound

HRID 922078Notes

Reaction equation

HRID 922078 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4](I)[CH:3]=1.CCCCCCC.[CH3:16][O:17][C:18]1[CH:26]=[C:25]2[C:21]([CH2:22][CH2:23][C:24]2=O)=[CH:20][CH:19]=1.Cl>C1COCC1>[CH3:16][O:17][C:18]1[CH:26]=[C:25]2[C:21](=[CH:20][CH:19]=1)[CH2:22][CH:23]=[C:24]2[C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([Br:1])[CH:3]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8900HeptaneHCID 11561Benzene, 1-bromo-3-iodo-HCID 3340366-Methoxy-1-Indanone

Product 1

HCID 71212557HCID 71212557, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1-bromo-3-iodobenzene (339 mmol) in 600 ml of anhydrous THF at −40° C. is added dropwise a 1 M n-dibutylmagnesium solution in heptane (185 mmol). 6-Methoxyindanone (154 mmol) is then added by small portions at −40° C. Stirring continues for 24 hours as the mixture returns to room temperature. After hydrolysis with 300 ml of 1 N HCl, the aqueous phase is extracted 2 times with ethyl acetate. The organic phases are combined, dried on sodium sulfate, concentrated and given form in isopropyl ether to obtain the expected product.

Workup

  1. customreturns to room temperature
  2. extractionthe aqueous phase is extracted 2 times with ethyl acetate
  3. customdried on sodium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-2545740ddbb442bb92d8f6fd74f8769c
Source dataset
uspto-grants-2016_03
Patent number
US09278143B2

Reaction notes

Loading…