N-bromobutanimide → HCID 21841544, compound

HRID 964171Notes

Reaction equation

HRID 964171 reaction equation
[CH2:1]([O:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([O:12][CH2:13][CH2:14][CH2:15][CH3:16])[CH:7]=1)[CH2:2][CH2:3][CH3:4].[Br:17]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl>[Br:17][C:11]1[CH:10]=[CH:9][C:8]([O:12][CH2:13][CH2:14][CH2:15][CH3:16])=[CH:7][C:6]=1[O:5][CH2:1][CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 110961901,3-dibutoxybenzene

Product 1

HCID 21841544HCID 21841544, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

80 g of 1,3-dibutoxybenzene (0.36 mol) are dissolved at room temperature in 100 ml of carbon tetrachloride. 64.25 g of N-bromosuccinimide (0.36 mol) are introduced in portions over 30 minutes such that the temperature can be maintained between 20° C. and 30° C. When the addition is complete, the mixture is stirred at room temperature for 1 hour. The reaction mixture is filtered over kieselguhr and the solvent is removed completely by concentration. The crude product (110 g) is fractionated on a 10 cm Vigreux column at 10-1 mbar. In this way, 65 g of 1-bromo-2,4-dibutoxybenzene with a boiling point of 112° C. at 10-1 mbar are obtained as a yellowish oil in 60% yield.

Workup

  1. temperaturecan be maintained between 20° C. and 30° C
  2. additionWhen the addition
  3. filtrationThe reaction mixture is filtered over kieselguhr
  4. customthe solvent is removed completely by concentration

Sources & evidence

ORD record
ord-f1fc2fc5c5f7457ab9898ca66bb22871
Source dataset
uspto-grants-1998_06
Patent number
US05767169

Reaction notes

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