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

HRID 391428노트

반응식

HRID 391428 반응식
[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

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 8003Pentane용매HCID 8028Tetrahydrofuran용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-826719df704b4db38ef3a8d109aa5460
출처 데이터셋
uspto-grants-2013_02
특허 번호
US08383821B2

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