2-Bromo-5-fluorobenzaldehyde → (2-Bromo-5-fluorophenyl)(phenyl)methanol

HRID 469548

反応式

HRID 469548 の反応式
[C:1]1([Mg]Br)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Br:9][C:10]1[CH:17]=[CH:16][C:15]([F:18])=[CH:14][C:11]=1[CH:12]=[O:13]>CCOCC.C1COCC1.CCOC(C)=O>[Br:9][C:10]1[CH:17]=[CH:16][C:15]([F:18])=[CH:14][C:11]=1[CH:12]([C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)[OH:13]

参加物

6

反応物 2

HCID 27733212-Bromo-5-fluorobenzaldehydeHCID 178418255HCID 178418255、化合物

生成物 1

HCID 61100031(2-Bromo-5-fluorophenyl)(phenyl)methanol収率 85.4%

試薬・触媒・溶媒 3

HCID 3283Diethyl Ether溶媒HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒

実験手順

A solution of PhMgBr (1M in THF, 2.60 mL, 2.60 mmol) was added dropwise to a −78° C. solution of 2-bromo-5-fluorobenzaldehyde (0.4742 g, 2.336 mmol) in Et2O (5 mL) and THF (1.3 mL), stirred for 15 minutes, allowed to warm to room temperature, stirred for 30 minutes, diluted with EtOAc, washed with water and saturated NH4Cl, dried (Na2SO4), and filtered. The residue was chromatographed on SiO2 (0-10% Et2O/hexanes) to give 561.0 mg of the title compound as a clear gum. 1H NMR (300 MHz, DMSO-d6) δ 7.60 (dd, 1H), 7.46 (dd, 1H), 7.21-7.36 (m, 5H), 7.10 (ddd, 1H), 6.21 (s, 1H), 5.88 (s, 1H).

後処理

  1. stirringstirred for 30 minutes
  2. washwashed with water and saturated NH4Cl
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. customThe residue was chromatographed on SiO2 (0-10% Et2O/hexanes)

出典と根拠

ORDレコード
ord-097feba1694346f3a3e17d9ca7868bc8
出典データセット
uspto-grants-2014_01
特許番号
US08629143B2

関連ノート

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