N-bromobutanimide → Ethyl 2-(4-bromomethylphenoxy)-2-methylpropionate

HRID 2058075Notes

Reaction equation

HRID 2058075 reaction equation
[C:1]1([CH3:16])[CH:6]=[CH:5][C:4]([O:7][C:8]([CH3:15])([CH3:14])[C:9]([O:11][CH2:12][CH3:13])=[O:10])=[CH:3][CH:2]=1.[Br:17]N1C(=O)CCC1=O>C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1.C(Cl)(Cl)(Cl)Cl>[Br:17][CH2:16][C:1]1[CH:6]=[CH:5][C:4]([O:7][C:8]([CH3:15])([CH3:14])[C:9]([O:11][CH2:12][CH3:13])=[O:10])=[CH:3][CH:2]=1

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 1531788Ethyl 2-methyl-2-(4-methylphenoxy)propanoate

Product 1

HCID 12870372Ethyl 2-(4-bromomethylphenoxy)-2-methylpropionateYield 67.5%

Reagents, catalysts & solvents 2

HCID 7187Benzoyl PeroxideCatalystHCID 5943Carbon TetrachlorideSolvent

Procedure

(a) A mixture of 20 g of ethyl 2-(p-tolyloxy)-2-methylpropionate, 17.7 g of N-bromosuccinimide, 0.2 g of benzoyl peroxide and 140 ml of anhydrous carbon tetrachloride is refluxed under heating for 4 hours. After the reaction, the reaction mixture is left to stand for cooling and washed with water. The carbon tetrachloride layer is dried and then concentrated. The resulting oily product (28 g) is distilled under reduced pressure to give 18.3 g of ethyl 2-(4-bromomethylphenoxy)-2-methylpropionate, bp 146° to 148° C./1-2 mmHg.

Workup

  1. temperatureis refluxed
  2. temperatureunder heating for 4 hours
  3. customAfter the reaction
  4. waitthe reaction mixture is left
  5. temperaturefor cooling
  6. washwashed with water
  7. dry with materialThe carbon tetrachloride layer is dried
  8. concentrationconcentrated
  9. distillationThe resulting oily product (28 g) is distilled under reduced pressure

Sources & evidence

ORD record
ord-ec106db9c730455e99d7402e9f187a82
Source dataset
uspto-grants-1980_07
Patent number
US04214094

Reaction notes

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