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

HRID 907969Notes

Reaction equation

HRID 907969 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-ed70e1a475bc4df487b3f639693c9f64
Source dataset
uspto-grants-2011_09
Patent number
US08012976B2

Reaction notes

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