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

HRID 623780
ノート
印刷プレビュー

反応式

HRID 623780 の反応式
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
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 962Water溶媒2 回
HCID 8028
Tetrahydrofuran
溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-3aa9920747214732a011c81784a7b4f6
出典データセット
uspto-grants-2016_04
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09302988B2

反応ノート

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