Hydrogen Bromide → 4-Bromo-3-iodotoluene

HRID 1750835노트

반응식

HRID 1750835 반응식
[I:1][C:2]1[CH:8]=[C:7]([CH3:9])[CH:6]=[CH:5][C:3]=1N.N([O-])=O.[Na+].[BrH:14]>O>[Br:14][C:3]1[CH:5]=[CH:6][C:7]([CH3:9])=[CH:8][C:2]=1[I:1]

참가 물질

5

반응물 3

HCID 260Hydrogen Bromide2회HCID 27640002-Iodo-4-methylanilineHCID 23668193Sodium Nitrite

생성물 1

HCID 162180884-Bromo-3-iodotoluene수율 81.8%

시약·촉매·용매 1

HCID 962Water용매3회

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온도
0 °C

실험 절차

2-Iodo-4-methylaniline (100 g, 450 mmol) was suspended in the mixture of water (200 mL) and HBr (48%, 300 mL). The mixture was refluxed for 15 min. Then the mixture was cooled to 0° C., and NaNO2 (31.05 g, 0.45 mol) in water (150 ml) was added dropwise at such a rate that the temperature did not exceed 5° C. The diazonium solution wad stirred for a further 30 min at 0-5° C. and then added slowly to a stirred mixture of CuBr (64.5 g, 0.45 mol) in HBr (48%, 250 mL) and water (250 ml) at room temperature. The mixture was poured into ice and extracted with CH2Cl2 (500 ml×3). The methylene chloride layer was washed with brine, dried over Na2SO4, and evaporated in vacuum to give the crude product (109 g, yield 81.8%). It can be further purified by column chromatography eluting with petroleum ether. MS: 297 [M+1]+.

후처리

  1. temperatureThe mixture was refluxed for 15 min
  2. customdid not exceed 5° C
  3. additionThe mixture was poured into ice
  4. extractionextracted with CH2Cl2 (500 ml×3)
  5. washThe methylene chloride layer was washed with brine
  6. dry with materialdried over Na2SO4
  7. customevaporated in vacuum

출처 및 근거

ORD 기록
ord-dac33939e40e4d5694ab3aed46535c9f
출처 데이터셋
uspto-grants-2015_10
특허 번호
US09156860B2

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