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

HRID 891952ノート

反応式

HRID 891952 の反応式
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]

参加物

7

反応物 4

HCID 313Hydrochloric AcidHCID 21531Triisopropyl borateHCID 133302273-Bromo-1,2-dihydronaphthaleneHCID 178418306HCID 178418306、化合物

生成物 1

HCID 221764573,4-Dihydronaphthalen-2-ylboronic acid収率 60%

試薬・触媒・溶媒 2

HCID 3283Diethyl Ether溶媒HCID 8003Pentane溶媒

反応条件

温度
-65 °C

実験手順

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−).

後処理

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

出典と根拠

ORDレコード
ord-ca0f343ecd7f41c3a9b6ca562240cf91
出典データセット
uspto-grants-2006_02
特許番号
US07005432B2

反応ノート

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