Hydrochloric Acid → 2'-Benzyloxy-biphenyl-2-boronic acid

HRID 269535

반응식

HRID 269535 반응식
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1Br)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CC(C)=O.C(=O)=O.[B:29](OC(C)C)([O:34]C(C)C)[O:30]C(C)C.Cl>O1CCCC1.C(OCC)C>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[C:15]1[C:16]([B:29]([OH:34])[OH:30])=[CH:17][CH:18]=[CH:19][CH:20]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

참가 물질

7

반응물 4

HCID 313Hydrochloric AcidHCID 21531Triisopropyl borateHCID 18522661Acetone cardiceHCID 587309892'-Benzyloxy-2-bromobiphenyl

생성물 1

HCID 587309902'-Benzyloxy-biphenyl-2-boronic acid수율 80%

시약·촉매·용매 2

HCID 3283Diethyl Ether용매HCID 8028Tetrahydrofuran용매

실험 절차

A solution of 2′-benzyloxy-2-bromobiphenyl (2.41 g, 7.09 mmol) in tetrahydrofuran (50 ml) was stirred under nitrogen and cooled to −100° C. (diethyl ether/liquid nitrogen). 1.6M nButyllithium in hexanes (4.87 ml, 7.80 mmol) was added over 15 mins. at −100° C. and the mixture warmed to −78° C. (acetone/Drikold) and stirred for 1 h. Triisopropyl borate (4.00 g (5.02 ml, 21.30 mmol) was added at −78° C. and the reaction allowed to warm to room temperature with stirring over 1.5 h. 1M Hydrochloric acid (50 ml) was added and the mixture stirred vigorously for 1 h. The organic layer was separated and the aqueous layer extracted with diethyl ether (50 ml). The combined organic phase were washed with water, dried (MgSO4) and the solvent removed in vacuo. The yellow oil was flash chromatographed (silica gel, 10-20% EtOAc-isohexane) to give the title compound as a clear oil (1.74 g, 80%). LC/MS RT=3.28 min [(2M−H2O)H−]=589.3

후처리

  1. stirringwith stirring over 1.5 h
  2. stirringthe mixture stirred vigorously for 1 h
  3. customThe organic layer was separated
  4. extractionthe aqueous layer extracted with diethyl ether (50 ml)
  5. washThe combined organic phase were washed with water
  6. dry with materialdried (MgSO4)
  7. customthe solvent removed in vacuo
  8. customchromatographed (silica gel, 10-20% EtOAc-isohexane)

출처 및 근거

ORD 기록
ord-212f4fc7464e40c4bd2bff88e26051d6
출처 데이터셋
uspto-grants-2008_11
특허 번호
US07446222B2

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