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

HRID 469548

반응식

HRID 469548 반응식
[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]

참가 물질

6

반응물 2

HCID 27733212-Bromo-5-fluorobenzaldehydeHCID 178418255HCID 178418255, 화합물

생성물 1

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

시약·촉매·용매 3

HCID 3283Diethyl Ether용매HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-097feba1694346f3a3e17d9ca7868bc8
출처 데이터셋
uspto-grants-2014_01
특허 번호
US08629143B2

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