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

HRID 333110노트

반응식

HRID 333110 반응식
[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]

참가 물질

6

반응물 4

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

생성물 1

HCID 866605416-Bromo-5,5,6,6-tetrafluorohexane cyclohexanecarboxylate수율 90%

시약·촉매·용매 1

HCID 962Water용매

실험 절차

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%.

후처리

  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

출처 및 근거

ORD 기록
ord-87df49ba21b446bc97b49990c2618151
출처 데이터셋
uspto-grants-2014_11
특허 번호
US08877960B2

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