Carbon tetrabromide → 1-Bromo-3-(1-bromoethyl)-5-fluorobenzene

HRID 391428ノート

反応式

HRID 391428 の反応式
[Br:1][C:2]1[CH:3]=[C:4]([CH:9](O)[CH3:10])[CH:5]=[C:6]([F:8])[CH:7]=1.C(Br)(Br)(Br)[Br:13].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>O1CCCC1.CCCCC>[Br:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[C:4]([CH:9]([Br:13])[CH3:10])[CH:3]=1

参加物

6

反応物 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 222402011-(3-Bromo-5-fluorophenyl)ethanol

生成物 1

HCID 589936681-Bromo-3-(1-bromoethyl)-5-fluorobenzene

試薬・触媒・溶媒 2

HCID 8003Pentane溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of (±)-1-(3-bromo-5-fluorophenyl)ethanol (1.0 g, 4.6 mmol) and carbon tetrabromide (1.82 g, 5.48 mmol) in tetrahydrofuran (5 mL) at 0° C. was added triphenylphosphine (1.44 g, 5.48 mmol). The resulting solution was stirred at room temperature for 45 min. The reaction was diluted with several volumes of pentane, and filtered to remove the undissolved solids which were discarded. The organics were concentrated and purified by column chromatography (1% ethyl acetate/hexanes) to give 1.26 g (98%) as a colorless oil. 1H-NMR (CDCl3, 500 MHz) δ 7.35 (s, 1H), 7.17 (m, 1H), 7.09 (m, 1H), 5.06 (q, J=7.0 Hz, 1H), 2.00 (d, J=7.0 Hz, 3H); 13C NMR (126 MHz, CDCl3) δ ppm 163.6, 161.6, 147.2 (m), 126.0 (m), 122.8, 122.7, 119.2, 119.0, 113.3, 113.1, 46.5, 26.7.

後処理

  1. filtrationfiltered
  2. customto remove the undissolved solids which
  3. concentrationThe organics were concentrated
  4. custompurified by column chromatography (1% ethyl acetate/hexanes)
  5. customto give 1.26 g (98%) as a colorless oil

出典と根拠

ORDレコード
ord-826719df704b4db38ef3a8d109aa5460
出典データセット
uspto-grants-2013_02
特許番号
US08383821B2

反応ノート

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