Water → (5-Bromo-2-fluoro-phenyl)-{4-[(triisopropylsilyl)-ethynyl]-phenyl}methanol

HRID 2263588

反応式

HRID 2263588 の反応式
C([Li])CCC.Br[C:7]1[CH:12]=[CH:11][C:10]([C:13]#[C:14][Si:15]([CH:22]([CH3:24])[CH3:23])([CH:19]([CH3:21])[CH3:20])[CH:16]([CH3:18])[CH3:17])=[CH:9][CH:8]=1.[Br:25][C:26]1[CH:27]=[CH:28][C:29]([F:34])=[C:30]([CH:33]=1)[CH:31]=[O:32].O>CCCCCC.O1CCCC1>[Br:25][C:26]1[CH:27]=[CH:28][C:29]([F:34])=[C:30]([CH:31]([C:7]2[CH:12]=[CH:11][C:10]([C:13]#[C:14][Si:15]([CH:22]([CH3:24])[CH3:23])([CH:19]([CH3:21])[CH3:20])[CH:16]([CH3:18])[CH3:17])=[CH:9][CH:8]=2)[OH:32])[CH:33]=1

参加物

7

反応物 4

HCID 962WaterHCID 7363275-Bromo-2-fluorobenzaldehydeHCID 57809595((4-Bromophenyl)ethynyl)triisopropylsilaneHCID 178418339Butyllithium

生成物 1

HCID 57809581(5-Bromo-2-fluoro-phenyl)-{4-[(triisopropylsilyl)-ethynyl]-phenyl}methanol

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒2 回HCID 8058Hexane溶媒

反応条件

温度
-78 °C

実験手順

33.8 ml of a 1.6 M solution of n-butyllithium in hexane are added dropwise under argon to a solution of 17.4 g 1-bromo-4-triisopropylsilylethynyl-benzene in 120 ml dry tetrahydrofuran chilled to −78° C. The solution is stirred for 1 h at −70° C. Then 10.8 g 5-bromo-2-fluoro-benzaldehyde dissolved in 30 ml of tetrahydrofuran are added dropwise over 15 min. The resulting solution is left in the cooling bath to warm up overnight to ambient temperature. Then water is added and the mixture is extracted with ethyl acetate. The combined organic phase are dried over sodium sulphate, and the solvent is removed. The residue is purified through silica gel (cyclohexane/ethyl acetate 4:1).

後処理

  1. additionare added dropwise over 15 min
  2. waitThe resulting solution is left in the cooling bath
  3. temperatureto warm up overnight to ambient temperature
  4. extractionthe mixture is extracted with ethyl acetate
  5. dry with materialThe combined organic phase are dried over sodium sulphate
  6. customthe solvent is removed
  7. customThe residue is purified through silica gel (cyclohexane/ethyl acetate 4:1)

出典と根拠

ORDレコード
ord-8054f41ef21e44f896bb7df00f31e0b4
出典データセット
uspto-grants-2010_12
特許番号
US07851602B2

関連ノート

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