1,3-Dibromobenzene → HCID 22613229, compound

HRID 844355Notes

Reaction equation

HRID 844355 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Br:8])[CH:3]=1.[Mg].[C:10]1(=[O:20])[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH2:13][CH2:12][CH2:11]1>C(OCC)C>[Br:8][C:4]1[CH:3]=[C:2]([C:10]2([OH:20])[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[CH2:13][CH2:12][CH2:11]2)[CH:7]=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 79271,3-DibromobenzeneHCID 107241-TetraloneHCID 5462224Magnesium2×

Product 1

HCID 22613229HCID 22613229, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

To a solution of 1 g (4.2 mmol) 1,3-dibromobenzene in 10 mL diethyl ether was added 0.096 g (4 mmol) magnesium metal turnings. This mixture was stirred until all of the magnesium was consumed, at which time 0.29 g (2 mmol) 1-tetralone was added dropwise in 2 mL diethyl ether. The reaction was then heated to reflux for 30 min, after which the cooled reaction was quenched with a 10% HCl solution and extracted three times with ethyl acetate. The combined organic layers were washed with water, brine, dried over anhydrous sodium sulphate, filtered, and the solvent removed in vacuo to afford the crude product which was used without further purification.

Workup

  1. temperatureThe reaction was then heated
  2. temperatureto reflux for 30 min
  3. customafter which the cooled reaction
  4. customwas quenched with a 10% HCl solution
  5. extractionextracted three times with ethyl acetate
  6. washThe combined organic layers were washed with water, brine
  7. dry with materialdried over anhydrous sodium sulphate
  8. filtrationfiltered
  9. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-14e870ef79aa4bdea36a3566ca3fdf39
Source dataset
uspto-grants-2002_04
Patent number
US06380249B1

Reaction notes

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