Hydrochloric Acid → Boronic acid, [4-[2-(phenylmethoxy)ethyl]phenyl]-

HRID 1457496

반응식

HRID 1457496 반응식
[CH2:1]([O:8][CH2:9][CH2:10][C:11]1[CH:16]=[CH:15][C:14](Br)=[CH:13][CH:12]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([Li])CCC.C([O:26][B:27](OC(C)C)[O:28]C(C)C)(C)C.Cl>C1COCC1>[CH2:1]([O:8][CH2:9][CH2:10][C:11]1[CH:16]=[CH:15][C:14]([B:27]([OH:28])[OH:26])=[CH:13][CH:12]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

참가 물질

6

반응물 4

HCID 313Hydrochloric AcidHCID 21531Triisopropyl borateHCID 219093031-(2-(Benzyloxy)ethyl)-4-bromobenzeneHCID 178418339Butyllithium

생성물 1

HCID 11543402Boronic acid, [4-[2-(phenylmethoxy)ethyl]phenyl]-수율 64%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

3.8 g (13.0 mmol) of 4-(2-benzyloxyethyl) phenylbromide and 30 ml of dry THF were cooled to -80° C., and 9.4 ml of n-butyllithium (1.65M) was dripped to it. Stirring at the foregoing temperature was performed for 3 hours, and then mixture solution of 5.68 g (30.2 mmol) of triisopropoxyboron and 15 ml of dry THF was dripped, and stirring at room temperature was performed for 13 hours. After the reactions had been completed, 15 ml of 10% hydrochloric acid was added, and extraction with ethyl acetate was performed. After the extracted solution was dried, the solvent was removed by filtration. Then, refining was performed with a silica gel column chromatography (developing solvent: toluene/ethyl acetate=20/1) so that 3.21 g of 4-(2-benzyloxyethyl) phenyl boronic acid was obtained (yield 64%).

후처리

  1. stirringstirring at room temperature
  2. waitwas performed for 13 hours
  3. extractionextraction with ethyl acetate
  4. customAfter the extracted solution was dried
  5. customthe solvent was removed by filtration
  6. customwas obtained (yield 64%)

출처 및 근거

ORD 기록
ord-b723b5d6be384cbaab574ef2a6a21752
출처 데이터셋
uspto-grants-1998_12
특허 번호
US05849217

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