Hydrochloric Acid → 3,4-Dihydronaphthalen-2-ylboronic acid

HRID 891952노트

반응식

HRID 891952 반응식
Br[C:2]1[CH2:3][CH2:4][C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2.C([Li])(C)(C)C.C([O:20][B:21](OC(C)C)[O:22]C(C)C)(C)C.Cl>C(OCC)C.CCCCC>[CH:11]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][C:2]=1[B:21]([OH:22])[OH:20]

참가 물질

7

반응물 4

HCID 313Hydrochloric AcidHCID 21531Triisopropyl borateHCID 133302273-Bromo-1,2-dihydronaphthaleneHCID 178418306HCID 178418306, 화합물

생성물 1

HCID 221764573,4-Dihydronaphthalen-2-ylboronic acid수율 60%

시약·촉매·용매 2

HCID 3283Diethyl Ether용매HCID 8003Pentane용매

반응 조건

온도
-65 °C

실험 절차

A solution of 3-bromo-1,2-dihydro-naphthalene (7.7 g, 37 mmol) (Adamczyk, M.; Watt, D. S.; Netzel, D. A. J. Org. Chem. 1984, 49, 4226-4237) in diethylether (370 ml) was cooled in a dry ice bath and tert.-butyllithium solution (50 ml of a 1.5 M solution in pentane) was added maintaining T<−65° C. At this temperature stirring was continued for 30 min, then triisopropylborate (17.3 ml, 75 mmol) was added. The reaction mixture was brought to rt and treated with 3N HCl (100 ml). After 15 min the organic phase was dried (Na2SO4), evaporated and precipitated with pentane to provide the title compound (3.83 g, 60%) as a white solid material. MS: m/e=173 (M−H−).

후처리

  1. customwas brought to rt
  2. dry with materialAfter 15 min the organic phase was dried (Na2SO4)
  3. customevaporated
  4. customprecipitated with pentane

출처 및 근거

ORD 기록
ord-ca0f343ecd7f41c3a9b6ca562240cf91
출처 데이터셋
uspto-grants-2006_02
특허 번호
US07005432B2

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