Water → HCID 46314739、化合物

HRID 659124ノート

反応式

HRID 659124 の反応式
Br[C:2]1[CH:3]=[CH:4][C:5]([F:10])=[C:6]([CH:9]=1)[C:7]#[N:8].[C:11]1(B(O)O)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.C([O-])([O-])=O.[Cs+].[Cs+].O>C1(C)C=CC=CC=1>[F:10][C:5]1[CH:4]=[CH:3][C:2]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[CH:9][C:6]=1[C:7]#[N:8]

参加物

6

反応物 4

HCID 962WaterHCID 10796Cesium carbonateHCID 66827Phenylboronic AcidHCID 27249005-Bromo-2-fluorobenzonitrile

生成物 1

HCID 46314739HCID 46314739、化合物

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

実験手順

5-Bromo-2-fluorobenzonitrile (53) (500 mg, 2.54 mmol) was coupled to phenylboronic acid (335 mg, 2.75 mmol) with Cs2CO3 (1.63 g, 5.00 mmol) in toluene (4 mL) in a microwave at 140° C. for 30 minutes. Water was added and the organics extracted several times with EtOAc, dried (MgSO4), filtered and the solvent concentrated in vacuo. The crude product was purified by Flash Master Jones Chromatography using a 25 g silica cartridge and eluting with 10% EtOAc in heptane to yield the title compound. Yield: 375 mg, 76%; LC-MS tr 1.63 min; HPLC Purity: 97%; MS (ES+) m/z not detectable (M+H)

後処理

  1. dry with materialthe organics extracted several times with EtOAc, dried (MgSO4)
  2. filtrationfiltered
  3. concentrationthe solvent concentrated in vacuo
  4. customThe crude product was purified by Flash Master Jones Chromatography
  5. washeluting with 10% EtOAc in heptane

出典と根拠

ORDレコード
ord-7bce9bd8947944bfb775552980f3b2a4
出典データセット
uspto-grants-2011_12
特許番号
US08080567B2

反応ノート

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