Bromine → 1-Bromo-2,5-difluoro-4-methylbenzene

HRID 1977851노트

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HRID 1977851 반응식
[F:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[CH3:9].[Br:10]Br>CCOCC.[Fe]>[Br:10][C:6]1[CH:7]=[C:2]([F:1])[C:3]([CH3:9])=[CH:4][C:5]=1[F:8]

참가 물질

5

반응물 2

HCID 24408BromineHCID 679802,5-Difluorotoluene

생성물 1

HCID 27829131-Bromo-2,5-difluoro-4-methylbenzene

시약·촉매·용매 2

HCID 23925Iron촉매HCID 3283Diethyl Ether용매

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온도
-5 °C

실험 절차

A mixture of 2,5-difluorotoluene (25 g, 0.20 mol) and iron powder (11 g, 0.2 mol) was cooled to −5° C. Bromine was added dropwise such that the internal temperature of the reaction did not rise above 0° C. After stirring for 3 hours, the mixture was diluted with ether, filtered and washed with aqueous sodium thiosulfate solution. The aqueous layer was extracted with ether, and the combined organic layers were dried over MgSO4, filtered and concentrated in vacuo. Distillation at atmospheric pressure gave 34 g of 1-bromo-2,5-difluoro-4-methyl-benzene as a colorless oil (b.p. 180° C.). 1H NMR (300 MHz, CDCl3) δ7.20 (dd, 1H, J=6.0, 8.5 Hz), 6.93 (m, 1H), 2.23 (s, 3H) ppm.

후처리

  1. customdid not rise above 0° C
  2. filtrationfiltered
  3. washwashed with aqueous sodium thiosulfate solution
  4. extractionThe aqueous layer was extracted with ether
  5. dry with materialthe combined organic layers were dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. distillationDistillation at atmospheric pressure

출처 및 근거

ORD 기록
ord-fa007ed0c804469484a83281e06d6e7a
출처 데이터셋
uspto-grants-2001_05
특허 번호
US06235764B1

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