Hexane → (6-Phenylnaphthalen-2-yl)boronic acid

HRID 1514006ノート

反応式

HRID 1514006 の反応式
Br[C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[CH:8]=2)[CH:3]=1.CCCCCC.C([Li])CCC.[B:29](OC(C)C)([O:34]C(C)C)[O:30]C(C)C>O.C1(C)C=CC=CC=1.C(OCC)C>[C:12]1([C:7]2[CH:8]=[C:9]3[C:4](=[CH:5][CH:6]=2)[CH:3]=[C:2]([B:29]([OH:34])[OH:30])[CH:11]=[CH:10]3)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

参加物

8

反応物 4

HCID 8058HexaneHCID 21531Triisopropyl borateHCID 153112152-Bromo-6-phenylnaphthaleneHCID 178418339Butyllithium

生成物 1

HCID 57539613(6-Phenylnaphthalen-2-yl)boronic acid収率 87.6%

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 1140Toluene溶媒2 回HCID 3283Diethyl Ether溶媒

反応条件

温度
-10 °C

実験手順

In an atmosphere of argon, 360 g (1.27 mol) of 2-bromo-6-phenylnaphthalene, 2 L of dehydrated diethyl ether and 2 L of dehydrated toluene were charged and cooled to −10° C. Then, 1 L (1.58 mol) of a hexane solution of 1.58M n-butyl lithium was added dropwise, and stirred at −10° C. for 5 hours. The reaction solution was cooled to −60° C., and after adding 718 g (3.81 mol) of triisopropyl borate, the mixture was stirred at room temperature for 17 hours. After adding 1 L of toluene and 1 L of water, the resulting mixture was stirred for an hour. Then, an aqueous layer was removed. An organic layer was washed with water, and dried with magnesium sulfate. The organic layer was concentrated, and heat-washed with toluene, whereby 276 g of 6-phenylnaphthalene-2-boronic acid was obtained (yield: 87%).

後処理

  1. temperatureThe reaction solution was cooled to −60° C.
  2. stirringthe mixture was stirred at room temperature for 17 hours
  3. stirringthe resulting mixture was stirred for an hour
  4. customThen, an aqueous layer was removed
  5. washAn organic layer was washed with water
  6. dry with materialdried with magnesium sulfate
  7. concentrationThe organic layer was concentrated
  8. washheat-washed with toluene

出典と根拠

ORDレコード
ord-2549a37f851d4cf98f5c8c97e59222d7
出典データセット
uspto-grants-2012_07
特許番号
US08221907B2

反応ノート

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