Water → 1-Bromo-4-(isocyanomethyl)-2-methylbenzene

HRID 1844632노트

반응식

HRID 1844632 반응식
[Br:1][C:2]1[CH:11]=[CH:10][C:5]([CH2:6][NH:7][CH:8]=O)=[CH:4][C:3]=1[CH3:12].P(Cl)(Cl)(Cl)=O.O.C(=O)([O-])O.[Na+]>ClCCl.C(OCC)(=O)C>[Br:1][C:2]1[CH:11]=[CH:10][C:5]([CH2:6][N+:7]#[C-:8])=[CH:4][C:3]=1[CH3:12]

참가 물질

7

반응물 4

HCID 962WaterHCID 24813Phosphorus oxychlorideHCID 516892Sodium BicarbonateHCID 58497978N-(4-bromo-3-methyl-benzyl)-formamide

생성물 1

HCID 584979501-Bromo-4-(isocyanomethyl)-2-methylbenzene수율 114.1%

시약·촉매·용매 2

HCID 6344Dichloromethane용매2회HCID 8857Ethyl Acetate용매

실험 절차

To a solution of N-(4-bromo-3-methyl-benzyl)-formamide (4.3 g) (Example I2) in dichloromethane (70 ml) was added a solution of phosphorus oxychloride (2.8 g) in dichloromethane (15 ml) at 0-5° C. The reaction mixture was stirred at ambient temperature for 16 hours. The reaction mixture was poured onto a mixture of ice and water (400 ml), and sodium hydrogen carbonate (saturated) (100 ml) and ethyl acetate (250 ml) were added. The phases were separated and the organic phase was washed with brine, dried over sodium sulfate and concentrated to give 1-bromo-4-isocyanomethyl-2-methyl-benzene (4.52 g) as a in brown oil. 1H-NMR (400 MHz, CDCl3): 7.54 (m, 1H), 7.22 (s, 1H), 7.03 (m, 1H), 4.57 (s, 2H), 2.42 (s, 3H) ppm.

후처리

  1. customat 0-5° C
  2. additionwere added
  3. customThe phases were separated
  4. washthe organic phase was washed with brine
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated

출처 및 근거

ORD 기록
ord-41f15bcfd21941ad90bcf965facb3905
출처 데이터셋
uspto-grants-2015_02
특허 번호
US08946447B2

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