Methyl 2-bromo-4-methylbenzoate → 1-(2-Bromo-4-methylphenyl)cyclopentanol

HRID 1037112ノート

反応式

HRID 1037112 の反応式
[Br:1][C:2]1[CH:11]=[C:10]([CH3:12])[CH:9]=[CH:8][C:3]=1[C:4]([O:6]C)=O.[Mg]([CH2:15][CH2:16][CH2:17][CH2:18][Mg]Br)Br>C1COCC1>[Br:1][C:2]1[CH:11]=[C:10]([CH3:12])[CH:9]=[CH:8][C:3]=1[C:4]1([OH:6])[CH2:18][CH2:17][CH2:16][CH2:15]1

参加物

4

反応物 2

HCID 21779704Methyl 2-bromo-4-methylbenzoateHCID 178419681HCID 178419681、化合物

生成物 1

HCID 726983321-(2-Bromo-4-methylphenyl)cyclopentanol収率 78%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of methyl 2-bromo-4-methylbenzoate (5.0 g, 21.3 mmol) in THF (20 mL) was added dropwise BrMg(CH2)4MgBr (50 mL, 25.5 mmol) at 0° C. under nitrogen and then stirred at rt overnight. The reaction mixture was quenched with aqueous NH4Cl and extracted with EA. The combined organic layer was washed with aqueous NaHCO3 solution and brine, dried over Na2SO4. The solution was concentrated and the residue was purified by column chromatography over silica gel eluted with PE-EA (20:110:1) to provide 1-(2-bromo-4-methylphenyl)-cyclopentanol (4.2 g; yield 78%) as a white solid. 1H NMR (400 MHz, DMSO-d6): δ 7.65 (d, 1 H), 7.39 (s, 1 H), 7.10 (d, 1 H), 4.84 (s, 1 H), 2.33 (s, 3 H), 1.89-1.74 (m, 8 H) ppm.

後処理

  1. customThe reaction mixture was quenched with aqueous NH4Cl
  2. extractionextracted with EA
  3. washThe combined organic layer was washed with aqueous NaHCO3 solution and brine
  4. dry with materialdried over Na2SO4
  5. concentrationThe solution was concentrated
  6. customthe residue was purified by column chromatography over silica gel
  7. washeluted with PE-EA (20:110:1)

出典と根拠

ORDレコード
ord-8b7fb9976eee497d965eb493f22d77a9
出典データセット
uspto-grants-2013_10
特許番号
US08546357B2

反応ノート

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