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Hydrochloric Acid → 1-Benzyl-3-bromo-4-methyl-5-(trifluoromethyl)-1H-pyrrole-2-carboxylic acid

HRID 623780
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HRID 623780 반응식
O.[OH-].[Li+].[CH2:4]([N:11]1[C:15]([C:16]([F:19])([F:18])[F:17])=[C:14]([CH3:20])[C:13]([Br:21])=[C:12]1[C:22]([O:24]CC)=[O:23])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.Cl>C1COCC1.O>[CH2:4]([N:11]1[C:15]([C:16]([F:17])([F:18])[F:19])=[C:14]([CH3:20])[C:13]([Br:21])=[C:12]1[C:22]([OH:24])=[O:23])[C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1
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참가 물질

6

반응물 3

HCID 313Hydrochloric AcidHCID 168937Lithium hydroxide, monohydrateHCID 86711864Ethyl 1-benzyl-3-bromo-4-methyl-5-(trifluoromethyl)-1H-pyrrole-2-carboxylate

생성물 1

HCID 867118651-Benzyl-3-bromo-4-methyl-5-(trifluoromethyl)-1H-pyrrole-2-carboxylic acid수율 85.5%

시약·촉매·용매 2

HCID 962Water용매2회
HCID 8028
Tetrahydrofuran
용매

실험 절차

Lithium hydroxide monohydrate (8.89 g, 371.6 mmol) was added to the ice cold solution of ethyl 1-benzyl-3-bromo-4-methyl-5-(trifluoromethyl)-1H-pyrrole-2-carboxylate (29 g, 74.32 mmol) in THF (300 mL) and H2O (100 mL) warmed to RT and then heated at 100° C. for 14 h, cooled to RT and then diluted with H2O and acidify with 6N HCl (pH-2). The aqueous layer was extracted with EtOAc (2×350 mL). Combined organic layer was dried over anhydrous Na2SO4, concentrated under reduced pressure to yield crude mass which was triturated with diethyl ether to afford title compound (23 g, 85.48% yield, white color solid).

후처리

  1. temperatureheated at 100° C. for 14 h
  2. temperaturecooled to RT
  3. extractionThe aqueous layer was extracted with EtOAc (2×350 mL)
  4. dry with materialCombined organic layer was dried over anhydrous Na2SO4
  5. concentrationconcentrated under reduced pressure
  6. customto yield crude mass which
  7. customwas triturated with diethyl ether

출처 및 근거

ORD 기록
ord-3aa9920747214732a011c81784a7b4f6
출처 데이터셋
uspto-grants-2016_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09302988B2

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