Hydrochloric Acid → 8-chloro-6-iodo-2-(trifluoromethyl)-2H-chromene-3-carboxylic Acid

HRID 854988

反応式

HRID 854988 の反応式
[Cl:1][C:2]1[CH:3]=[C:4]([I:21])[CH:5]=[C:6]2[C:11]=1[O:10][CH:9]([C:12]([F:15])([F:14])[F:13])[C:8]([C:16]([O:18]CC)=[O:17])=[CH:7]2.O[Li].O.Cl>C1COCC1.CO.O>[Cl:1][C:2]1[CH:3]=[C:4]([I:21])[CH:5]=[C:6]2[C:11]=1[O:10][CH:9]([C:12]([F:14])([F:13])[F:15])[C:8]([C:16]([OH:18])=[O:17])=[CH:7]2

参加物

5

反応物 3

HCID 313Hydrochloric AcidHCID 168937Lithium hydroxide, monohydrateHCID 58934641ethyl 8-chloro-6-iodo-2-(trifluoromethyl)-2H-chromene-3-carboxylate

生成物 1

HCID 117740818-chloro-6-iodo-2-(trifluoromethyl)-2H-chromene-3-carboxylic Acid収率 88.3%

試薬・触媒・溶媒 1

HCID 21892291Methanol tetrahydrofuran water溶媒

実験手順

To 180 mg (0.42 mmole) of ethyl 8-chloro-6-iodo-2-(trifluoromethyl)-2H-chromene-3-carboxylate was added 100 mgs of LiOH—H2O and 5 mL of a solvent mixture of THF/MeOH/H2O (7:2:1). The mixture was heated to reflux for 30 min. and allowed to cool to rt. After standing overnight, the mixture was concd in vacuo, treated with 20 mL 1N HCl and allowed to stir. The mixture was extracted three times with Et2O, the combined extracts dried and concd in vacuo to give 150 mgs (88.3%) of an off-white solid: 1H NMR (CDCl3/d6-acetone/400 MHz) 5.86 (q, 1H, J=6.7 Hz), 7.60 (s, 1H), 7.70 (s, 1H), 7.75 (s, 1H); 19F NMR (CDCl3/d6-acetone/400 MHz) −79.2 (d, 3F, J=6.8 Hz); MS(ESI+) 405 (M+1, 100, one Cl pattern); HRMS (ES-) m/z calcd for (C11H4O3IClF3) 402.8840, found 402.8850.

後処理

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 30 min.
  3. extractionThe mixture was extracted three times with Et2O
  4. customthe combined extracts dried

出典と根拠

ORDレコード
ord-e0b50e65fafd4b0d9935d996c4c18b2f
出典データセット
uspto-grants-2007_08
特許番号
US07259266B2

関連ノート

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