2-Bromopropane → 4-Bromo-2-chloro-1-isopropoxybenzene

HRID 1942640Notes

Reaction equation

HRID 1942640 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[C:4]([Cl:9])[CH:3]=1.C([O-])([O-])=O.[K+].[K+].Br[CH:17]([CH3:19])[CH3:18]>CN(C)C=O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH:17]([CH3:19])[CH3:18])=[C:4]([Cl:9])[CH:3]=1

Participants

5

Reactant 3

HCID 63582-BromopropaneHCID 11430Potassium CarbonateHCID 198594-Bromo-2-chlorophenol

Product 1

HCID 219385904-Bromo-2-chloro-1-isopropoxybenzene

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
85 °C

Procedure

To a solution of 4-bromo-2-chlorophenol (50 g) in N,N-dimethylformamide (DMF) (250 mL) stirred under nitrogen at room temperature was added K2CO3 (100 g) and 2-bromopropane (136 mL) in one charge. The reaction mixture was stirred at 85° C. for 16 h. After cooling the reaction, the reaction mixture was filtered, the solvent of the filtrate was removed in vacuo. The residue was dissolved in diethyl ether (300 mL), washed with water (6*100 mL), the organic phase was dried over MgSO4 and concentrated to give 4-bromo-2-chlorophenyl 1-methylethyl ether (D68) (56 g) as a yellow oil. δH (CDCl3, 400 MHz): 1.37 (6H, d), 4.52 (1H, m), 6.82 (1H, d), 7.29 (1H, m), 7.50 (1H, d).

Workup

  1. additioncharge
  2. temperatureAfter cooling
  3. customthe reaction
  4. filtrationthe reaction mixture was filtered
  5. customthe solvent of the filtrate was removed in vacuo
  6. dissolutionThe residue was dissolved in diethyl ether (300 mL)
  7. washwashed with water (6*100 mL)
  8. dry with materialthe organic phase was dried over MgSO4
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-e8f9cd1fd21648fa9279ed990d7ec3a8
Source dataset
uspto-grants-2013_03
Patent number
US08389508B2

Reaction notes

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