Tetrahydrofuran → 6-Bromo-5,5,6,6-tetrafluorohexane cyclohexanecarboxylate

HRID 333110ノート

反応式

HRID 333110 の反応式
[CH:1]1([C:7](Cl)=[O:8])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[O:10]1CCCC1.[Br:15][C:16]([F:26])([F:25])[C:17]([F:24])([F:23])[CH2:18][CH2:19][CH2:20][CH2:21]O.C(N(CC)CC)C>O>[CH:1]1([C:7]([OH:8])=[O:10])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[Br:15][C:16]([F:25])([F:26])[C:17]([F:23])([F:24])[CH2:18][CH2:19][CH2:20][CH3:21]

参加物

6

反応物 4

HCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 75938Cyclohexanecarbonyl chlorideHCID 232369226-Bromo-5,5,6,6-tetrafluorohexan-1-ol

生成物 1

HCID 866605416-Bromo-5,5,6,6-tetrafluorohexane cyclohexanecarboxylate収率 90%

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

A 300 mL reactor was charged under nitrogen with 14.7 g (100 mmol/1.3 equivalents) of cyclohexanecarbonyl chloride and 150 mL of tetrahydrofuran (a dehydrated product), followed by putting it in an ice bath. 20.0 g (79.0 mmol/1.0 equivalent) of 6-bromo-5,5,6,6-tetrafluorohexan-1-ol was added thereto, followed by adding dropwise of 12.0 g (119 mmol/1.5 equivalents) of triethylamine. After the dropping, stirring was conducted at 60 degrees for 6 hours. Then, 100 mL of water was added, and extraction was conducted two times with 200 mL of diisopropyl ether. The obtained organic layer was washed further with diluted hydrochloric acid, sodium bicarbonate water and brine, followed by removing water by sodium sulfate and conducting filtration. Then, isopropyl ether was distilled out, thereby obtaining 27.5 g of the target 6-bromo-5,5,6,6-tetrafluorohexane cyclohexanecarboxylate. Upon this, purity was 94%, and yield was 90%.

後処理

  1. extractionextraction
  2. washThe obtained organic layer was washed further with diluted hydrochloric acid, sodium bicarbonate water and brine
  3. customby removing water by sodium sulfate
  4. filtrationfiltration
  5. distillationThen, isopropyl ether was distilled out

出典と根拠

ORDレコード
ord-87df49ba21b446bc97b49990c2618151
出典データセット
uspto-grants-2014_11
特許番号
US08877960B2

反応ノート

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