N-bromobutanimide → 1-(Benzyloxy)-4-bromo-2-ethyl-5-methoxybenzene

HRID 392864Notes

Reaction equation

HRID 392864 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([O:17][CH3:18])[CH:12]=[CH:13][C:14]=1[CH2:15][CH3:16])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Br:19]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl>[CH2:1]([O:8][C:9]1[C:14]([CH2:15][CH3:16])=[CH:13][C:12]([Br:19])=[C:11]([O:17][CH3:18])[CH:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 226620992-(Benzyloxy)-1-ethyl-4-methoxybenzene

Product 1

HCID 226621061-(Benzyloxy)-4-bromo-2-ethyl-5-methoxybenzene

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

In a bromination reaction, the 3-benzyloxy-4-ethyl-1-methoxybenzene (3) is combined with N-bromosuccinimide (NBS) and silica gel 60 (EM Science, 480 Democrat Road, Gibbstown, N.J. 08027, an affiliate of Merck KGaA, Darmstadt, Germany) in a nonpolar solvent such as carbon tetrachloride at a temperature from about 0° C. to about room temperature. Preferably, the reaction is conducted at about room temperature. This reaction is allowed to stir, in the absence of light, to yield 5-benzyloxy-2-bromo-4-ethyl-1-methoxybenzene (4).

Workup

  1. customIn a bromination reaction
  2. customfrom about 0° C. to about room temperature
  3. customis conducted at about room temperature

Sources & evidence

ORD record
ord-5ee50cd272504f13b1988b21ab1465e4
Source dataset
uspto-grants-2004_10
Patent number
US06803470B2

Reaction notes

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