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Carbon tetrabromide → Tert-butyl [2-(2-bromoethyl)-2,3-dihydro-2,4,6,7-tetramethylbenzofuran-5-yl]carbamate

HRID 565664
ノート
印刷プレビュー

反応式

HRID 565664 の反応式
O[CH2:2][CH2:3][C:4]1([CH3:24])[CH2:8][C:7]2[C:9]([CH3:23])=[C:10]([NH:15][C:16](=[O:22])[O:17][C:18]([CH3:21])([CH3:20])[CH3:19])[C:11]([CH3:14])=[C:12]([CH3:13])[C:6]=2[O:5]1.C(Br)(Br)(Br)[Br:26].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>O1CCCC1>[Br:26][CH2:2][CH2:3][C:4]1([CH3:24])[CH2:8][C:7]2[C:9]([CH3:23])=[C:10]([NH:15][C:16](=[O:22])[O:17][C:18]([CH3:21])([CH3:20])[CH3:19])[C:11]([CH3:14])=[C:12]([CH3:13])[C:6]=2[O:5]1
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 54463969Tert-butyl [2,3-dihydro-2-(2-hydroxyethyl)-2,4,6,7-tetramethylbenzofuran-5-yl]carbamate

生成物 1

HCID 54438432Tert-butyl [2-(2-bromoethyl)-2,3-dihydro-2,4,6,7-tetramethylbenzofuran-5-yl]carbamate収率 82%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran
溶媒

実験手順

To a solution of tert-butyl [2,3-dihydro-2-(2-hydroxyethyl)-2,4,6,7-tetramethylbenzofuran-5-yl]carbamate (7.7 g) and carbon tetrabromide (8.0 g) in tetrahydrofuran (80 mL) was added 6.3 g of triphenylphosphine under ice-cooling and the mixture was stirred for 30 minutes. This reaction mixture was filtered and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=97:3 to 4:1) to provide 7.5 g of the title compound. Yield 82%.

後処理

  1. temperaturecooling
  2. filtrationThis reaction mixture was filtered
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=97:3 to 4:1)

出典と根拠

ORDレコード
ord-7eda659980da4537aa82588395baa004
出典データセット
uspto-grants-2001_01
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06172085B2

反応ノート

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