Hydrochloric Acid → (5,5,8,8-Tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)boronic acid

HRID 858263ノート

反応式

HRID 858263 の反応式
[CH3:1][C:2]1([CH3:15])[CH2:11][CH2:10][C:9]([CH3:13])([CH3:12])[C:8]2[CH:7]=[C:6](Br)[CH:5]=[CH:4][C:3]1=2.C([Li])CCC.[B:21](OC(C)C)([O:26]C(C)C)[O:22]C(C)C.Cl>C1COCC1>[CH3:1][C:2]1([CH3:15])[CH2:11][CH2:10][C:9]([CH3:13])([CH3:12])[C:8]2[CH:7]=[C:6]([B:21]([OH:26])[OH:22])[CH:5]=[CH:4][C:3]1=2

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 21531Triisopropyl borateHCID 2266856-Bromo-1,1,4,4-tetramethyl-1,2,3,4-tetrahydronaphthaleneHCID 178418339Butyllithium

生成物 1

HCID 10353857(5,5,8,8-Tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)boronic acid

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

21.38 g (80.0 mmol) of 5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-bromonaphthalene and 50 ml of THF are introduced into a three-necked flask under a stream of nitrogen. 38.4 ml (96.0 mmol) of n-butyllithium (2.5 M in hexane) are added dropwise, at −78° C., and the mixture is stirred for one hour. 27.7 ml (120.0 mmol) of triisopropyl borate are added dropwise at this same temperature and the mixture is stirred for 2 hours. 350 ml of hydrochloric acid (1 N) are added at −50° C. and the mixture is allowed to warm to room temperature. The reaction medium is extracted with dichloromethane and the organic phase is separated out after settling has taken place, dried over magnesium sulphate and evaporated. 18.60 g (100%) of the expected boronic acid are collected in the form of an oil which crystallizes slowly. Melting point 190–192° C.

後処理

  1. stirringthe mixture is stirred for 2 hours
  2. extractionThe reaction medium is extracted with dichloromethane
  3. customthe organic phase is separated out after settling
  4. dry with materialdried over magnesium sulphate
  5. customevaporated
  6. custom18.60 g (100%) of the expected boronic acid are collected in the form of an oil which
  7. customcrystallizes slowly

出典と根拠

ORDレコード
ord-e33e3d049de54c90a613e71b7c64c9e1
出典データセット
uspto-grants-2006_12
特許番号
US07148245B2

反応ノート

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