Sodium Cyanide → 1-(3-Bromo-4-fluorophenyl)-1-cyanomethanol

HRID 272657

반응식

HRID 272657 반응식
S(=O)(O)[O-].[Na+].[Br:6][C:7]1[CH:8]=[C:9]([CH:12]=[CH:13][C:14]=1[F:15])[CH:10]=[O:11].[C-:16]#[N:17].[Na+]>O.CCOCC>[Br:6][C:7]1[CH:8]=[C:9]([CH:10]([C:16]#[N:17])[OH:11])[CH:12]=[CH:13][C:14]=1[F:15]

참가 물질

6

반응물 3

HCID 8929Sodium CyanideHCID 1736043-Bromo-4-fluorobenzaldehydeHCID 23665763Sodium Bisulfite

생성물 1

HCID 434366161-(3-Bromo-4-fluorophenyl)-1-cyanomethanol수율 92%

시약·촉매·용매 2

HCID 962Water용매HCID 3283Diethyl Ether용매

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온도
50 °C

실험 절차

A solution of sodium bisulfite (28.3 g, 271 mmol) in water at 50° C. is treated with 3-bromo-4-fluorobenzaldehyde (45.8 g, 225 mmol), stirred at 50° C. for 2 h, cooled with an ice bath, diluted with ether, treated dropwise with an aqueous solution of sodium cyanide (12.2 g, 248 mmol) over a period of 30 min and stirred at room temperature overnight. The reaction mixture is separated, and the aqueous phase is extracted with ether. The extracts are combined with the organic phase, washed with brine, dried over magnesium sulfate and concentrated to dryness to afford the title compound as a clear oil, 47.6 g (92% yield), identified by NMR analysis. 1H NMR (300 MHz, CDCl3) δ 7.75 (m, 1H), 7.47 (m, 1H), 7.23 (m, 1H), 5.54 (m, 1H), 3.19 (m, 1H).

후처리

  1. temperaturecooled with an ice bath
  2. stirringstirred at room temperature overnight
  3. customThe reaction mixture is separated
  4. extractionthe aqueous phase is extracted with ether
  5. washwashed with brine
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated to dryness

출처 및 근거

ORD 기록
ord-6d1b69fd37f049abab1d5c9a36b457bc
출처 데이터셋
uspto-grants-2008_11
특허 번호
US07456186B2

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