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

HRID 432221

반응식

HRID 432221 반응식
[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]

참가 물질

4

반응물 2

HCID 262953-Phenoxybenzyl alcoholHCID 67184N-bromobutanimide

생성물 1

HCID 22346758(2-Bromo-5-phenoxyphenyl)methanol수율 85%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-e6881106d19a47819921a3fd29407149
출처 데이터셋
uspto-grants-2003_12
특허 번호
US06660744B1

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