Toluene → 1,3-Dibromo-5-isobutoxybenzene

HRID 1513119Notes

Reaction equation

HRID 1513119 reaction equation
[OH-].[K+].[Br:3][C:4]1[CH:5]=[C:6]([OH:11])[CH:7]=[C:8]([Br:10])[CH:9]=1.[C:12]1([CH3:18])[CH:17]=CC=C[CH:13]=1.BrCCCCC>O.[Cl-].C([N+](CCCC)(CCCC)CCCC)C1C=CC=CC=1>[Br:3][C:4]1[CH:5]=[C:6]([O:11][CH2:13][CH:12]([CH3:18])[CH3:17])[CH:7]=[C:8]([Br:10])[CH:9]=1

Participants

7

Reactant 4

HCID 1140TolueneHCID 80571-BromopentaneHCID 122803,5-DibromophenolHCID 14797Potassium Hydroxide

Product 1

HCID 508527731,3-Dibromo-5-isobutoxybenzene

Reagents, catalysts & solvents 2

HCID 159952Benzyltributylammonium chlorideCatalystHCID 962WaterSolvent

Conditions

Temperature
85 °C

Procedure

Potassium hydroxide (15.9 g; 284 mmol) was dissolved in water (300 ml) and 3,5-dibromo-phenol (47 g; 188.5 mmol) was added. Benzyl tributylammoniumchloride (17.7 g; 56.8 mmol) and toluene (200 ml) was added and the reaction mixture was heated to 85° C. Bromoethylpropan (32.3 g; 325.7 mmol) was added over 5 hours and the reaction mixture was stirred at 85° C. for additional 16 h. The reaction mixture was cooled to room temperature and the phases were separated. Toluene (100 ml) was added to the organic phase which was washed with 0.2 N aqueous HCl (200 ml×2) and water (200 ml×2). The organic phase was evaporated to give the crude product which was purified by distillation (0.7. mm Hg; Bp: 98° C.); Yield: 43 g (colourless oil).

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. customthe phases were separated
  3. additionToluene (100 ml) was added to the organic phase which
  4. washwas washed with 0.2 N aqueous HCl (200 ml×2) and water (200 ml×2)
  5. customThe organic phase was evaporated

Sources & evidence

ORD record
ord-724e4795b9e5439197434ead48b65a0d
Source dataset
uspto-grants-2012_07
Patent number
US08217086B2

Reaction notes

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