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

HRID 1457498

반응식

HRID 1457498 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 71%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

13.7 g (47.1 mmol) of 4-(2-benzyloxyethyl) phenylbromide and 80 ml of dry THF were cooled to -75° C., and 34.0 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 12.9 g (68.7 mmol) of triisopropoxyboron and 50 ml of dry THF was dripped, and stirring at -75° C. was performed for 2 hours and that at room temperature was performed for 14 hours. After the reactions had been completed, 50 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 8.62 g of 4-(2-benzyloxyethyl) phenyl boronic acid was obtained (yield 71%).

후처리

  1. stirringstirring at -75° C.
  2. waitwas performed for 2 hours and that at room temperature
  3. waitwas performed for 14 hours
  4. extractionextraction with ethyl acetate
  5. customAfter the extracted solution was dried
  6. customthe solvent was removed by filtration
  7. customwas obtained (yield 71%)

출처 및 근거

ORD 기록
ord-78d4712c72084bc4b4fdf152e90d9420
출처 데이터셋
uspto-grants-1998_12
특허 번호
US05849217

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