N-bromobutanimide → Ethyl 2-bromomethyl-6-methoxybenzoate

HRID 1582281Notes

Reaction equation

HRID 1582281 reaction equation
[CH3:1][O:2][C:3]1[CH:13]=[CH:12][CH:11]=[C:10]([CH3:14])[C:4]=1[C:5]([O:7][CH2:8][CH3:9])=[O:6].[Br:15]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl.C(OCC)C.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>[Br:15][CH2:14][C:10]1[C:4]([C:5]([O:7][CH2:8][CH3:9])=[O:6])=[C:3]([O:2][CH3:1])[CH:13]=[CH:12][CH:11]=1

Participants

6

Reactant 2

HCID 67184N-bromobutanimideHCID 5910602-Methoxy-6-methyl-benzoic acid ethyl ester

Product 1

HCID 10038926Ethyl 2-bromomethyl-6-methoxybenzoateYield 60%

Reagents, catalysts & solvents 3

HCID 7187Benzoyl PeroxideCatalystHCID 3283Diethyl EtherSolventHCID 5943Carbon TetrachlorideSolvent

Procedure

To a solution of ethyl 2-methoxy-6-methylbenzoate (0.813 g, 4.19 mmol) in CCl4 (8 mL) was added recrystallized N-bromosuccinimide (0.751 g, 4.22 mmol) followed by benzoyl peroxide (52 mg, 0.22 mmol). The resultant mixture was heated to reflux for 90 minutes then cooled to room temperature. The mixture was diluted with diethyl ether (50 mL), filtered through filter paper, and the filtrate was concentrated. Purification of the crude material by column chromatography (8:1 hexanes-EtOAc) provided 0.68 g (60%) of ethyl 6-(bromomethyl)-2-methoxybenzoate as a colorless oil. 1NMR (CDCl3) δ1.42 (t, 3H, J=7.2 Hz), 3.84 (s, 3H), 4.45 (q, 2H, J=7.2 Hz), 4.50 (s, 2H), 6.89 (d, 1H, J=8.4 Hz), 7.01 (d, 1H, J=7.2 Hz), 7.34 (dd, 1H, J=7.2, 8.4 Hz).

Workup

  1. temperatureto reflux for 90 minutes
  2. filtrationfiltered
  3. filtrationthrough filter paper
  4. concentrationthe filtrate was concentrated
  5. customPurification of the crude material by column chromatography (8:1 hexanes-EtOAc)

Sources & evidence

ORD record
ord-193aa351dd594061a6acbfe6c8f8f84f
Source dataset
uspto-grants-2004_05
Patent number
US06734191B2

Reaction notes

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