3-Phenoxybenzyl alcohol → (2-Bromo-5-phenoxyphenyl)methanol

HRID 432221

反応式

HRID 432221 の反応式
[O:1]([C:8]1[CH:9]=[C:10]([CH2:14][OH:15])[CH:11]=[CH:12][CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Br:16]N1C(=O)CCC1=O>C(#N)C>[Br:16][C:11]1[CH:12]=[CH:13][C:8]([O:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)=[CH:9][C:10]=1[CH2:14][OH:15]

参加物

4

反応物 2

HCID 262953-Phenoxybenzyl alcoholHCID 67184N-bromobutanimide

生成物 1

HCID 22346758(2-Bromo-5-phenoxyphenyl)methanol収率 85%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

To a solution of 3-phenoxyphenyl methanol (4.0 g, 0.020 mol) in anhydrous acetonitrile was added 1-bromo-2,5-pyrrolidinedione (3.73 g, 0.021 mol) at room temperature. The mixture was stirred at room temperature for one and a half hour under an atmosphere of nitrogen. The solvents were removed under the reduced pressure. Tetrachloromethane (100 mL) was added to the residue, and the mixture was filtered. The filtrate was concentrated into the residue, and the residue was purified by flash chromatography on silica gel using ethyl acetate/n-heptane (1:5) as mobile phase to yield (2-bromo-5-phenoxyphenyl)methanol (4.7 g, 0.017 mol): RP-HPLC (Hypersil C18, 5 μm, 250×4.6 mm; 25%-100% over 10 min with 0.1 M ammonium acetate, 1 mL/min) Rt 11.7 min. TLC (ethyl acetate/heptane 1:5) Rf 0.18.

後処理

  1. customThe solvents were removed under the reduced pressure
  2. additionTetrachloromethane (100 mL) was added to the residue
  3. filtrationthe mixture was filtered
  4. concentrationThe filtrate was concentrated into the residue
  5. customthe residue was purified by flash chromatography on silica gel

出典と根拠

ORDレコード
ord-e6881106d19a47819921a3fd29407149
出典データセット
uspto-grants-2003_12
特許番号
US06660744B1

関連ノート

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