1-Benzyloxy-4-bromo-2-fluoro-5-nitrobenzene → 4-(benzyloxy)-7-bromo-5-fluoro-1H-indole

HRID 2421229ノート

反応式

HRID 2421229 の反応式
[Br:1][C:2]1[CH:7]=[C:6]([F:8])[C:5]([O:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[CH:4][C:3]=1[N+:17]([O-])=O.[CH:20]([Mg]Br)=[CH2:21]>C1COCC1>[Br:1][C:2]1[CH:7]=[C:6]([F:8])[C:5]([O:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[C:4]2[C:3]=1[NH:17][CH:21]=[CH:20]2

参加物

4

反応物 2

HCID 583039441-Benzyloxy-4-bromo-2-fluoro-5-nitrobenzeneHCID 178418507HCID 178418507、化合物

生成物 1

HCID 583038564-(benzyloxy)-7-bromo-5-fluoro-1H-indole収率 34.7%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
-40 °C

実験手順

A solution of 1-bromo-5-fluoro-2-nitro-4-[(phenylmethyl)oxy]benzene (D4) (10.58 g, 32.4 mmol) in THF was cooled to −40° C. under argon and vinylmagnesium bromide (97 mL of 1M solution in THF, 97 mmol) was added quickly via syringe. The temperature reached ˜−30° C. before cooling down to −40° C. The mixture was stirred at −40° C. for 40 mins and then quenched by the addition of NH4Cl solution. The mixture was allowed to reach room temperature and the layers were separated. The aqueous layer was reextracted with ethyl acetate and the combined organic layers were dried (Na2SO4) and evaporated. Chromatography on silica gel (elution with 0-50% ethyl acetate in hexane) gave the title compound as an orange oil (D5), (3.6 g).

後処理

  1. customreached ˜−30° C.
  2. customquenched by the addition of NH4Cl solution
  3. customto reach room temperature
  4. customthe layers were separated
  5. dry with materialthe combined organic layers were dried (Na2SO4)
  6. customevaporated

出典と根拠

ORDレコード
ord-c9b235a31db94f6b9a4dbfcf0deb848d
出典データセット
uspto-grants-2011_06
特許番号
US07956083B2

反応ノート

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