Hydrochloric Acid → 2-Bromo-3-fluoro-6-nitrophenol

HRID 1731812ノート

反応式

HRID 1731812 の反応式
[Br:1][C:2]1[C:3](F)=[C:4]([N+:9]([O-:11])=[O:10])[CH:5]=[CH:6][C:7]=1[F:8].[OH-].[K+].CC[O:17]CC.Cl>CS(C)=O.O>[Br:1][C:2]1[C:3]([OH:17])=[C:4]([N+:9]([O-:11])=[O:10])[CH:5]=[CH:6][C:7]=1[F:8]

参加物

7

反応物 4

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 14797Potassium HydroxideHCID 137327452-Bromo-1,3-difluoro-4-nitrobenzene

生成物 1

HCID 137328542-Bromo-3-fluoro-6-nitrophenol収率 93%

試薬・触媒・溶媒 2

HCID 679Dimethyl Sulfoxide溶媒HCID 962Water溶媒

実験手順

A solution of 3-bromo-2,4-difluoro-1-nitrobenzene (10.5 g, 44 mmol) in dimethyl sulfoxide (85 ml) was stirred at ambient temperature. A solution of potassium hydroxide (14.1 g, 251 mmol) in water (21 ml) was added dropwise over 15 minutes. The black reaction mixture was stirred at ambient temperature for 16 hours. The reaction mixture was then poured onto water (200 ml) and three ether extractions (100 ml) were performed. The aqueous layer was acidified with concentrated hydrochloric acid and extracted three times with ether (100 ml). The combined organic layers were dried over magnesium sulfate and filtered. Solvent was removed in vacuo to give a yellow solid (9.7 g, 93% yield). Recrystallization from isopropyl ether afforded an analytical sample: m.p. 65°-66° C. NMR (CDCl3, 60 MHz): 8.1 (dd, 1H, J=10, 5 Hz), 6.8 (dd, 1H, J=10, 8 Hz)

後処理

  1. customThe black reaction mixture
  2. extractionextracted three times with ether (100 ml)
  3. dry with materialThe combined organic layers were dried over magnesium sulfate
  4. filtrationfiltered
  5. customSolvent was removed in vacuo

出典と根拠

ORDレコード
ord-169c70f529384da2ae8d398e36c8b332
出典データセット
uspto-grants-1986_11
特許番号
US04623650

反応ノート

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