Water → Methyl 2-(bromomethyl)-5-chloro-3-nitrobenzoate

HRID 1467707Notes

Reaction equation

HRID 1467707 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([N+:13]([O-:15])=[O:14])[C:5]([CH3:12])=[C:6]([CH:11]=1)[C:7]([O:9][CH3:10])=[O:8].C1C(=O)N([Br:23])C(=O)C1.O>C(Cl)(Cl)(Cl)Cl>[Br:23][CH2:12][C:5]1[C:4]([N+:13]([O-:15])=[O:14])=[CH:3][C:2]([Cl:1])=[CH:11][C:6]=1[C:7]([O:9][CH3:10])=[O:8]

Participants

5

Reactant 3

HCID 962WaterHCID 67184N-bromobutanimideHCID 53399191Methyl 5-chloro-2-methyl-3-nitrobenzoate

Product 1

HCID 67258857Methyl 2-(bromomethyl)-5-chloro-3-nitrobenzoateYield 87%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

A mixture of methyl 5-chloro-2-methyl-3-nitrobenzoate (6 g, 26.2 mmol), NBS (5.1 g, 28.8 mmol), and BPO (0.63 g, 2.6 mmol) in CCl4 (50 mL) was heated to reflux overnight. Water (200 mL) was added and CCl4 was removed under reduced pressure. The residue was extracted with DCM (200 mL×3). The combined organic layers were washed with brine, dried over Na2SO4, and concentrated to give crude title compound (7 g, yield 87%) as a brown oil which was used in the next step without purification.

Workup

  1. temperaturewas heated
  2. temperatureto reflux overnight
  3. customCCl4 was removed under reduced pressure
  4. extractionThe residue was extracted with DCM (200 mL×3)
  5. washThe combined organic layers were washed with brine
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-98e4d19311764d66b0720d61df99927a
Source dataset
uspto-grants-2015_04
Patent number
US08999987B2

Reaction notes

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