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

HRID 979019

반응식

HRID 979019 반응식
[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]

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 5943Carbon Tetrachloride용매2회

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-cb2a61df9ae04d58bf5f8019560e5004
출처 데이터셋
uspto-grants-1987_05
특허 번호
US04666820

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