N-bromobutanimide → Methyl 4-(bromomethyl)-3-nitrobenzoate

HRID 435143

Reaction equation

HRID 435143 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([CH3:11])=[C:7]([N+:12]([O-:14])=[O:13])[CH:6]=1)=[O:4].[Br:15]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl>[CH3:1][O:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([CH2:11][Br:15])=[C:7]([N+:12]([O-:14])=[O:13])[CH:6]=1)=[O:4]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 81816Methyl 4-methyl-3-nitrobenzoate

Product 1

HCID 13399987Methyl 4-(bromomethyl)-3-nitrobenzoate

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent2×

Procedure

All of the 4-methoxycarbonyl-2-nitrotoluene obtained as described above was dissolved in carbon tetrachloride. Approximately 14.2 g (0.082 mole) of N-bromosuccinimide was added to the carbon tetrachloride solution. The resulting solution was heated to reflux temperature and stirred for approximately 64 hours. The solution was cooled and the succinimide was removed by vacuum filtration. The remaining solution was concentrated on a rotary evaporator using water aspirator vacuum. The synthesis produced 24 g of 4-methoxycarbonyl-2-nitrobenzyl bromide. The cholate ester of this product was then prepared as described for the preparation of the esters in Section B. The O,O,O-triacetyl derivative was also prepared as described in Section F.

Workup

  1. temperatureThe resulting solution was heated
  2. temperatureto reflux temperature
  3. temperatureThe solution was cooled
  4. customthe succinimide was removed by vacuum filtration
  5. concentrationThe remaining solution was concentrated on a rotary evaporator

Sources & evidence

ORD record
ord-2098fbb8c47a4459a83564039f42c795
Source dataset
uspto-grants-1983_08
Patent number
US04400461

Linked notes

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