N-bromobutanimide → Methyl 4-(bromomethyl)-2-methoxybenzoate

HRID 59314Notes

Reaction equation

HRID 59314 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[C:11]([CH3:13])[CH:10]=[CH:9][C:4]=1[C:5]([O:7][CH3:8])=[O:6].C1C(=O)N([Br:21])C(=O)C1>C(Cl)(Cl)(Cl)Cl.C(OCC)C.CC(N=NC(C#N)(C)C)(C#N)C>[Br:21][CH2:13][C:11]1[CH:10]=[CH:9][C:4]([C:5]([O:7][CH3:8])=[O:6])=[C:3]([O:2][CH3:1])[CH:12]=1

Participants

6

Reactant 2

HCID 67184N-bromobutanimideHCID 7172021Methyl 2-methoxy-4-methylbenzoate

Product 1

HCID 11288398Methyl 4-(bromomethyl)-2-methoxybenzoateYield 70.2%

Reagents, catalysts & solvents 3

HCID 6547AzobisisobutyronitrileCatalystHCID 3283Diethyl EtherSolventHCID 5943Carbon TetrachlorideSolvent

Procedure

To a solution of methyl 2-methoxy-4-methylbenzoate (10.00 g, 55 mmol) in CCl4 (150 mL) were added NBS (11.8 g, 66 mmol) and AIBN (0.100 g). The reaction mixture was refluxed for 18 h. The reaction mass was diluted with diethyl ether and washed with 25% NaOH solution. The organic layer was dried over anhydrous sodium sulphate and concentrated to afford 10.00 g of desired product. 1H NMR (300 MHz, DMSO d6): δ 3.77 (m, 6H), 4.68 (s, 2H), 7.06 (d, J=7.8 Hz, 1H), 7.23 (s, 1H), 7.61 (d, J=7.8 Hz, 1H); MS (m/z): 259.13 (M)+.

Workup

  1. temperatureThe reaction mixture was refluxed for 18 h
  2. washwashed with 25% NaOH solution
  3. dry with materialThe organic layer was dried over anhydrous sodium sulphate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-6d9a70ba4d3d4031a7a8f9ca00e906c1
Source dataset
uspto-grants-2016_09
Patent number
US09439890B2

Reaction notes

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