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

HRID 1712137ノート

反応式

HRID 1712137 の反応式
[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]

参加物

5

反応物 2

HCID 24408BromineHCID 679802,5-Difluorotoluene

生成物 1

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

試薬・触媒・溶媒 2

HCID 23925Iron触媒HCID 3283Diethyl Ether溶媒

反応条件

温度
-5 °C

実験手順

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) δ 7.20 (dd, 1H, J=6.0, 8.5 Hz), 6.93 (m, 1H), 2.23 (s, 3H) ppm.

後処理

  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

出典と根拠

ORDレコード
ord-2f345a5ee7ef4e88a2bfb39279dde47f
出典データセット
uspto-grants-2010_09
特許番号
US07790902B2

反応ノート

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