Bromocyclopentane → Methyl 3-cyclopentyloxy-4-nitrobenzoate

HRID 356924노트

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HRID 356924 반응식
[CH:1]1(Br)[CH2:5][CH2:4][CH2:3][CH2:2]1.C(=O)([O-])[O-].[K+].[K+].[OH:13][C:14]1[CH:15]=[C:16]([CH:21]=[CH:22][C:23]=1[N+:24]([O-:26])=[O:25])[C:17]([O:19][CH3:20])=[O:18]>CN(C)C=O>[CH:1]1([O:13][C:14]2[CH:15]=[C:16]([CH:21]=[CH:22][C:23]=2[N+:24]([O-:26])=[O:25])[C:17]([O:19][CH3:20])=[O:18])[CH2:5][CH2:4][CH2:3][CH2:2]1

참가 물질

5

반응물 3

HCID 8728BromocyclopentaneHCID 11430Potassium CarbonateHCID 294866Methyl 3-hydroxy-4-nitrobenzoate

생성물 1

HCID 21187961Methyl 3-cyclopentyloxy-4-nitrobenzoate수율 102.2%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

Cyclopentyl bromide (38.7 g, 0.26 mol) is added slowly (over 1 hour) to a stirred suspension of potassium carbonate (41.4 g, 0.3 mol) in N,N-dimethylformamide (200 mL) containing methyl 3-hydroxy-4-nitrobenzoate (39.4 g, 0.2 mol) at 65° C. and then the stirring is continued for 4 hours. The mixture is allowed to cool and then filtered. The filtrate is diluted with water (700 mL) containing sodium chloride (50 g) and then extracted with toluene (3×200 mL). The combined organic extract is washed with 1 N sodium hydroxide solution (1×200 mL) and then water (2×200 mL) and then evaporated under reduced pressure to give methyl 3-cyclopentyloxy-4-nitrobenzoate (54.2 g, 100%) as a pale green solid which is used without further purification.

후처리

  1. temperatureto cool
  2. filtrationfiltered
  3. additionThe filtrate is diluted with water (700 mL)
  4. additioncontaining sodium chloride (50 g)
  5. extractionextracted with toluene (3×200 mL)
  6. extractionThe combined organic extract
  7. washis washed with 1 N sodium hydroxide solution (1×200 mL)
  8. customwater (2×200 mL) and then evaporated under reduced pressure

출처 및 근거

ORD 기록
ord-445b41f90eec4e948b3fe16dfc8ac900
출처 데이터셋
uspto-grants-1998_11
특허 번호
US05840724

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