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Hydrochloric Acid → (3-Bromo-2-fluorophenyl)boronic acid

HRID 1018402
ノート
印刷プレビュー

反応式

HRID 1018402 の反応式
C([Li])CCC.[Br:6][C:7]1[CH:12]=[CH:11][CH:10]=[C:9](Br)[C:8]=1[F:14].[B:15](OC)([O:18]C)[O:16]C.Cl>CCCCCC.C(OCC)C.O>[Br:6][C:7]1[C:8]([F:14])=[C:9]([B:15]([OH:18])[OH:16])[CH:10]=[CH:11][CH:12]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

8

反応物 4

HCID 313Hydrochloric AcidHCID 8470Trimethyl borateHCID 140714601,3-Dibromo-2-fluorobenzeneHCID 178418339Butyllithium

生成物 1

HCID 16217170(3-Bromo-2-fluorophenyl)boronic acid

試薬・触媒・溶媒 3

HCID 962Water溶媒
HCID 3283
Diethyl Ether
溶媒
HCID 8058Hexane溶媒

実験手順

290 ml of a 1.6 molar solution of butyllithium in hexane are added dropwise at −70° C. to a solution of 112 g of 2,6-dibromofluorobenzene [1435-54-7] in 1000 ml of diethyl ether. After the mixture has been kept at the same temperature for 2 hours, 60 ml of trimethyl borate are added, and the mixture is stirred at this temperature for 12 hours. After the mixture has been slowly warmed to room temperature, 300 ml of water are added, and the pH is adjusted to 1 by addition of hydrochloric acid. The organic phase is separated off, the aqueous phase is extracted twice with 100 ml of ether each time, and the combined organic phases are dried under reduced pressure, giving 91 g of 3-bromo-2-fluorophenylboronic acid (mixed with its cyclic anhydride) as a brown solid; 1H-NMR (DMSO-d6): 7.1-7.7 (m) ppm, 19F-NMR (DMSO-d6): −99 ppm.

後処理

  1. customThe organic phase is separated off
  2. extractionthe aqueous phase is extracted twice with 100 ml of ether each time
  3. customthe combined organic phases are dried under reduced pressure

出典と根拠

ORDレコード
ord-6d2e62cd092b4c0c8def6d7daa57c2c9
出典データセット
uspto-grants-2002_11
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06482478B1

反応ノート

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