3,4-Dichlorophenol → 4-(3-Bromopropoxy)-1,2-dichlorobenzene

HRID 2121070Notes

Reaction equation

HRID 2121070 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([OH:9])[CH:5]=[CH:6][C:7]=1[Cl:8].[Br:10][CH2:11][CH2:12][CH2:13]Br.[OH-].[Na+]>S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC>[Cl:1][C:2]1[CH:3]=[C:4]([CH:5]=[CH:6][C:7]=1[Cl:8])[O:9][CH2:13][CH2:12][CH2:11][Br:10]

Participants

5

Reactant 3

HCID 72583,4-DichlorophenolHCID 80011,3-DibromopropaneHCID 14798Sodium Hydroxide

Product 1

HCID 117810424-(3-Bromopropoxy)-1,2-dichlorobenzene

Reagents, catalysts & solvents 1

HCID 94433Tetrabutylammonium hydrogen sulfateCatalyst

Conditions

Temperature
60 °C

Procedure

A mixture of 3,4-dichlorophenol (499.4 g. 3.06 moles), 1,3-dibromopropane (2424 ml, 12 moles), 24% sodium hydroxide (613 g, 3.83 moles), and 5 g of tetrabutylammonium hydrogen sulfate were stirred and heated at 50-70° C. for 2 h. The temperature was raised to 80° and heating was continued for 16 hr more. After cooling the lower phase was separated and excess dibromopropane was removed on a rotary evaporator. The residue was distilled through a short vigreux column at 1 mm vacuum. A total of 870 g (87.3%) of product was collected at 125-135° C. 1H-NMR (CDCl3) & 2.23 (m, 2H), 3.50 (t, 2H), 4.02 (t, 2H), 6.7-7.2 (m, 4H).

Workup

  1. temperatureThe temperature was raised to 80°
  2. temperatureheating
  3. temperatureAfter cooling the lower phase
  4. customwas separated
  5. customexcess dibromopropane was removed on a rotary evaporator
  6. distillationThe residue was distilled through a short vigreux column at 1 mm vacuum
  7. customA total of 870 g (87.3%) of product was collected at 125-135° C

Sources & evidence

ORD record
ord-d19eb55a890245b78f9fabed329051d8
Source dataset
uspto-grants-2004_02
Patent number
US06693217B2

Reaction notes

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