Diethyl Ether → Adamantane-1-ylmethyl bromodifluoroacetate

HRID 2219800노트

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HRID 2219800 반응식
[C:1]12([CH2:11][OH:12])[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.C(OCC)C.[Br:18][C:19]([F:24])([F:23])[C:20](Cl)=[O:21].C(N(CC)CC)C>O>[Br:18][C:19]([F:24])([F:23])[C:20]([O:12][CH2:11][C:1]12[CH2:8][CH:7]3[CH2:6][CH:5]([CH2:4][CH:3]([CH2:9]3)[CH2:2]1)[CH2:10]2)=[O:21]

참가 물질

6

반응물 4

HCID 3283Diethyl EtherHCID 8471TriethylamineHCID 64556Tricyclo(3.3.1.1'3,7)dec-1-ylmethanolHCID 520892Bromodifluoroacetyl chloride

생성물 1

HCID 46900814Adamantane-1-ylmethyl bromodifluoroacetate수율 95%

시약·촉매·용매 1

HCID 962Water용매

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온도
0 °C

실험 절차

A 200 mL, three-necked flask was charged with 4.76 g (31.8 mmol, 1.11 equivalents) of 1-adamantane methanol and 55 g of diethyl ether, followed by stirring to obtain a suspension. Then, 6.15 g (28.6 mmol, 1.0 equivalent) of bromodifluoroacetic chloride were added thereto. The resulting suspension was cooled down to 0° C. by using an iced bath, followed by adding 5.78 g (57.2 mmol, 2.0 equivalents) of triethylamine in a slow dropwise manner. This reaction liquid was allowed to stand with stirring to reach room temperature, followed by stirring at room temperature for 1 hour. Then, 50 g of water were added to wash the reaction liquid. The resulting organic layer was washed with 50 g of saturated sodium hydrogencarbonate, 50 g of saturated brine, and 50 g of water in sequence. Then, it was dried with magnesium sulfate, followed by distilling the solvent off, thereby obtaining 8.78 g of the target adamantane-1-ylmethyl bromodifluoroacetate (yield: 95%, purity: 100%).

후처리

  1. customto obtain a suspension
  2. customThis reaction liquid
  3. stirringwith stirring
  4. customto reach room temperature
  5. stirringby stirring at room temperature for 1 hour
  6. washto wash
  7. customthe reaction liquid
  8. washThe resulting organic layer was washed with 50 g of saturated sodium hydrogencarbonate, 50 g of saturated brine, and 50 g of water in sequence
  9. dry with materialThen, it was dried with magnesium sulfate
  10. distillationby distilling the solvent off,

출처 및 근거

ORD 기록
ord-c645125a9b9140bfb9dda74c7b49045e
출처 데이터셋
uspto-grants-2008_08
특허 번호
US07414148B2

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