Triethylamine → Adamantane-1-ylmethyl bromodifluoroacetate

HRID 84975

반응식

HRID 84975 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.[Br:13][C:14]([F:19])([F:18])[C:15](Cl)=[O:16].C(N(CC)CC)C>C(OCC)C>[C:1]12([CH2:11][O:12][C:15](=[O:16])[C:14]([Br:13])([F:19])[F:18])[CH2:8][CH:7]3[CH2:6][CH:5]([CH2:4][CH:3]([CH2:9]3)[CH2:2]1)[CH2:10]2

참가 물질

5

반응물 3

HCID 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 3283Diethyl Ether용매

반응 조건

온도
0 °C

실험 절차

Into a 50-L reaction vessel, 476 g (3.18 mol, 1.11 eq) of 1-adamantanemethanol and 5.5 kg of diethyl ether were added. The resulting solution was suspended by stirring, followed by adding thereto 615 g (2.86 mol, 1.0 eq) of bromodifluoroacetyl chloride. The suspended solution was cooled down to 0° C. Then, 578 g (5.72 mol, 2.0 eq) of triethylamine was slowly dropped to the cooled suspended solution. This reaction solution was left, while stirring, until it reached room temperature. The reaction solution was further stirred for 1 hour at room temperature. Subsequently, the reaction solution was washed with 5 kg of water. The thus-obtained organic layer was washed with 5 kg of saturated sodium hydrogencarbonate solution, with 5 kg of saturated sodium chloride solution, and then, with 5 kg of water. The washed organic layer was dried with magnesium sulfate and subjected to solvent distillation. With this, 878 g of target bromodifluoroacetic acid adamantane-1-ylmethyl ester was obtained (yield: 95%, purity: 100%).

후처리

  1. additionwere added
  2. additionby adding
  3. waitThis reaction solution was left
  4. stirringwhile stirring, until it
  5. customreached room temperature
  6. stirringThe reaction solution was further stirred for 1 hour at room temperature
  7. washSubsequently, the reaction solution was washed with 5 kg of water
  8. washThe thus-obtained organic layer was washed with 5 kg of saturated sodium hydrogencarbonate solution, with 5 kg of saturated sodium chloride solution
  9. dry with materialThe washed organic layer was dried with magnesium sulfate
  10. distillationsubjected to solvent distillation

출처 및 근거

ORD 기록
ord-4fce67bffe8f4b49ab3b92037c204409
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08846966B2

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