N-bromobutanimide → Methyl 4-bromomethyl-2-methoxymethoxybenzoate

HRID 2081882Notes

Reaction equation

HRID 2081882 reaction equation
[CH3:1][O:2][CH2:3][O:4][C:5]1[CH:14]=[C:13]([CH3:15])[CH:12]=[CH:11][C:6]=1[C:7]([O:9][CH3:10])=[O:8].[Br:16]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>[Br:16][CH2:15][C:13]1[CH:12]=[CH:11][C:6]([C:7]([O:9][CH3:10])=[O:8])=[C:5]([O:4][CH2:3][O:2][CH3:1])[CH:14]=1

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 13149247Methyl 2-(methoxymethoxy)-4-methylbenzoate

Product 1

HCID 19936849Methyl 4-bromomethyl-2-methoxymethoxybenzoateYield 101.9%

Reagents, catalysts & solvents 2

HCID 7187Benzoyl PeroxideCatalystHCID 5943Carbon TetrachlorideSolvent

Procedure

To a solution of methyl 2-methoxymethoxy-4-methylbenzoate (9.41 g, 0.0448 mol) in 150 mL of carbon tetrachloride was added N-bromosuccinimide (7.97 g, 0.0448 mol) and benzoyl peroxide (0.45 g, 0.002 mol). The reaction mixture was refluxed for 18 hours. The solid was filtered and the filtrate was concentrated in vacuo to give 13.2 g of an oil. The product was purified by flash chromatography on silica gel eluting with 20% ethyl acetate in hexane to give 10.2 g (79%) of product as an oil.

Workup

  1. temperatureThe reaction mixture was refluxed for 18 hours
  2. filtrationThe solid was filtered
  3. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-ca7bd9f3a77e4d98b9393a6b829f0492
Source dataset
uspto-grants-1993_02
Patent number
US05185351

Reaction notes

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