N-bromobutanimide → HCID 69585501, compound

HRID 2188009Notes

Reaction equation

HRID 2188009 reaction equation
[Br:1]N1C(=O)CCC1=O.N(C1(C#N)CCCCC1)=NC1(C#N)CCCCC1.[CH3:27][O:28][C:29](=[O:41])[C:30]1[CH:35]=[CH:34][CH:33]=[C:32]([O:36][CH2:37][O:38][CH3:39])[C:31]=1[CH3:40]>C(Cl)(Cl)(Cl)Cl>[CH3:27][O:28][C:29](=[O:41])[C:30]1[CH:35]=[CH:34][CH:33]=[C:32]([O:36][CH2:37][O:38][CH3:39])[C:31]=1[CH2:40][Br:1]

Participants

5

Reactant 3

HCID 67184N-bromobutanimideHCID 749781,1'-Azobis(cyclohexanecarbonitrile)HCID 69585958HCID 69585958, compound

Product 1

HCID 69585501HCID 69585501, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

In a 25 ml round-bottom flask, N-bromo succinimide (236 mg, 1.3 mmol) and azobis(cyclohexanecarbonitrile) (33 mg, 0.14 mmol) were added to a solution of 3-methoxymethoxy-2-methyl-benzoic acid methyl ester (265 mg, 1.26 mmol) in carbon tetrachloride (6.5 ml). The reaction was heated to reflux with stirring for 3.5 hours. The volatiles were removed in vacuo and the residue purified by silica gel chromatography using a mixture of hexanes/ethyl acetate (9:1) as eluent, which afforded 364 mg (100%) of 2-bromomethyl-3-methoxymethoxy-benzoic acid methyl ester as a solid.

Workup

  1. temperatureThe reaction was heated
  2. temperatureto reflux
  3. customThe volatiles were removed in vacuo
  4. customthe residue purified by silica gel chromatography
  5. additiona mixture of hexanes/ethyl acetate (9:1) as eluent

Sources & evidence

ORD record
ord-e1290eee02a049f4802f5688d5203436
Source dataset
uspto-grants-2002_06
Patent number
US06410556B1

Reaction notes

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