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

HRID 269535

反応式

HRID 269535 の反応式
[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

参加物

7

反応物 4

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

生成物 1

HCID 587309902'-Benzyloxy-biphenyl-2-boronic acid収率 80%

試薬・触媒・溶媒 2

HCID 3283Diethyl Ether溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

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

後処理

  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)

出典と根拠

ORDレコード
ord-212f4fc7464e40c4bd2bff88e26051d6
出典データセット
uspto-grants-2008_11
特許番号
US07446222B2

関連ノート

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