Methanol → Methyl 4-(bromomethyl)-3-nitrobenzoate

HRID 1514940Notes

Reaction equation

HRID 1514940 reaction equation
[Br:1][CH2:2][C:3]1[CH:11]=[CH:10][C:6]([C:7]([OH:9])=[O:8])=[CH:5][C:4]=1[N+:12]([O-:14])=[O:13].CO.[CH2:17]1CCC(N=C=NC2CCCCC2)CC1>CN(C1C=CN=CC=1)C.C(Cl)Cl>[CH3:17][O:8][C:7](=[O:9])[C:6]1[CH:10]=[CH:11][C:3]([CH2:2][Br:1])=[C:4]([N+:12]([O-:14])=[O:13])[CH:5]=1

Participants

6

Reactant 3

HCID 887MethanolHCID 10868DicyclohexylcarbodiimideHCID 1323864-Bromomethyl-3-nitrobenzoic acid

Product 1

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

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-bromomethyl-3-nitrobenzoic acid (2.6 g, 10 mmol), MeOH (320 mg, 10 mmol) and DMAP (122 mg, 1 mmol) in methylene chloride (40 mL) was added DCC (2.06 g, 10 mmol) and the resulting mixture was stirred at ambient temperature for 2 h. The resulting precipitate was filtered and the filtrate evaporated under reduced pressure. The resulting oil was filtered through a plug of silica gel using methylene chloride as eluent. The solvent was removed under reduced pressure to give 4-bromomethyl-3-nitrobenzoic acid methyl ester as a pale-yellow oil.

Workup

  1. filtrationThe resulting precipitate was filtered
  2. customthe filtrate evaporated under reduced pressure
  3. filtrationThe resulting oil was filtered through a plug of silica gel
  4. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-76b2278c6d0043eba2840d0f9f439816
Source dataset
uspto-grants-2012_07
Patent number
US08222248B2

Reaction notes

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