N-bromobutanimide → HCID 69585501, compound

HRID 1242088Notes

Reaction equation

HRID 1242088 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-bromosuccinimide (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-61f1fdc99a9644039322e35dd4d32f5c
Source dataset
uspto-grants-2006_10
Patent number
US07115624B1

Reaction notes

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