Hydrochloric Acid → (3,4-Dihydroxyphenyl)boronic acid

HRID 1751169ノート

反応式

HRID 1751169 の反応式
Br[C:2]1[CH:3]=[C:4]([OH:9])[C:5](=[CH:7][CH:8]=1)[OH:6].[Li]CCCC.[B:15](OC)([O:18]C)[O:16]C.Cl>C1COCC1>[OH:9][C:4]1[CH:3]=[C:2]([B:15]([OH:18])[OH:16])[CH:8]=[CH:7][C:5]=1[OH:6]

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 8470Trimethyl borateHCID 284874-BromocatecholHCID 178418339Butyllithium

生成物 1

HCID 57416308(3,4-Dihydroxyphenyl)boronic acid収率 63.4%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

4-Bromocatechol (T-1) (18.8 g; made by Tokyo Chemical Industry Co., Ltd.) was dissolved in dry THF (200 ml), which was cooled to −70° C. n-BuLi (72 ml) was added under an atmosphere of nitrogen and the stirring was continued at −70° C. for 2 hours. Trimethyl borate (15.6 g) in a THF solution was then slowly added dropwise at −70° C., and the mixture was warmed to room temperature and stirred for 16 hours. After the completion of the reaction, 2N HCl (100 ml) was added and the mixture was extracted with toluene. The extract was washed with water and brine, and dried over anhydrous magnesium sulfate. The extract was concentrated under reduced pressure to give pale brown solids. The solids were recrystallized (heptane:toluene=4:1 by volume) to give 3,4-dihydroxyphenylboronic acid (T-2; 9.7 g; yield 63%) as colorless crystals.

後処理

  1. additionwas added under an atmosphere of nitrogen
  2. additionwas added
  3. extractionthe mixture was extracted with toluene
  4. washThe extract was washed with water and brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationThe extract was concentrated under reduced pressure
  7. customto give pale brown solids
  8. customThe solids were recrystallized (heptane:toluene=4:1 by volume)

出典と根拠

ORDレコード
ord-fff9240641b34d10a22bee33806707b5
出典データセット
uspto-grants-2015_10
特許番号
US09157027B2

反応ノート

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