Carbon tetrabromide → 2,2,3,3,4,4,4-heptafluoro-N-[4-(2-bromoethyl)phenyl]butanamide

HRID 35025

反応式

HRID 35025 の反応式
[F:1][C:2]([F:22])([C:15]([F:21])([F:20])[C:16]([F:19])([F:18])[F:17])[C:3]([NH:5][C:6]1[CH:11]=[CH:10][C:9]([CH2:12][CH2:13]O)=[CH:8][CH:7]=1)=[O:4].C(Br)(Br)(Br)[Br:24].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.P>O1CCCC1.C(OCC)C>[F:1][C:2]([F:22])([C:15]([F:21])([F:20])[C:16]([F:19])([F:18])[F:17])[C:3]([NH:5][C:6]1[CH:11]=[CH:10][C:9]([CH2:12][CH2:13][Br:24])=[CH:8][CH:7]=1)=[O:4]

参加物

7

反応物 4

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 24404PhosphineHCID 212977062,2,3,3,4,4,4-heptafluoro-N-[4-(2-hydroxyethyl)phenyl]butanamide

生成物 1

HCID 212977022,2,3,3,4,4,4-heptafluoro-N-[4-(2-bromoethyl)phenyl]butanamide収率 54.5%

試薬・触媒・溶媒 2

HCID 3283Diethyl Ether溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

A mixture of 2,2,3,3,4,4,4-heptafluoro-N-[4-(2-hydroxyethyl)phenyl]butanamide (25 g), carbon tetrabromide (51 g), diethyl ether (140 mL) and tetrahydrofuran (140 mL) was cooled in ice and treated with triphenylphosphine (39.3 g), portionwise. When addition of the phosphine was complete, the reaction mixture was allowed to warm to room temperature and stirred for 2 hours. The precipitate was removed by filtration and the filtrate concentrated in vacuo. The residue was purified by chromatography on silica gel, eluted with dichloromethane to give 16.2 g of 2,2,3,3,4,4,4-heptafluoro-N-[4-(2-bromoethyl)phenyl]butanamide as a white solid.

後処理

  1. temperaturewas cooled in ice
  2. customThe precipitate was removed by filtration
  3. concentrationthe filtrate concentrated in vacuo
  4. customThe residue was purified by chromatography on silica gel
  5. washeluted with dichloromethane

出典と根拠

ORDレコード
ord-4dd549727dfd4ba6bb0cc01ce71d4299
出典データセット
uspto-grants-1988_08
特許番号
US04764623

関連ノート

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