Water → 3-Benzoyloxy-4-fluorobenzyl bromide

HRID 19936

반응식

HRID 19936 반응식
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][C:3]=1[O:9][C:10](=[O:17])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.[Br:18]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1.O>C(Cl)(Cl)(Cl)Cl.C(OCC)C>[Br:18][CH2:8][C:5]1[CH:6]=[CH:7][C:2]([F:1])=[C:3]([O:9][C:10](=[O:17])[C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH:4]=1

참가 물질

7

반응물 4

HCID 962WaterHCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 167492203-Benzoyloxy-4-fluorotoluene

생성물 1

HCID 167478383-Benzoyloxy-4-fluorobenzyl bromide

시약·촉매·용매 2

HCID 3283Diethyl Ether용매HCID 5943Carbon Tetrachloride용매

실험 절차

A mixture of benzoic acid 2-fluoro-5-methyl-phenyl ester (CAB02145, 2.47 g, 10.0 mmol), N-bromo-succinimide (1.96 g, 11.0 mmol) and dibenzoylperoxide (10 mg) in carbon tetrachloride (25 mL) was heated to reflux for 2 h (TLC monitored). After cooling to room temperature, water (50 mL) and diethyl ether (100 mL) were added. The organic layer was separated, washed with brine (20 mL), dried over sodium sulphate and concentrated under reduced pressure. The residue was purified by column chromatography (EtOAc:hexane, 1:25, Rf: 0.28). Yield: 1.80 g (58%), white solid. 1H-NMR (400 MHz, CDCl3) δ=4.48 (s, 2H, —CH2Br), 7.18 (dd, J=9.8, 8.6 Hz, 1H), 7.28 (ddd, J=8.6, 4.3, 2.3 Hz, 1H), 7.34 (dd, J=7.0, 2.3 Hz, 1H), 7.50-7.55 (m, 2H), 7.64-7.69 (m, 1H), 8.18-8.23 (m, 2H). LRMS (FAB+): 229.1 (95), 309.0 (100, [M+]+). Found: C, 54.1, H, 3.22%; C14H10BrFO2 (309.13) requires C, 54.39, H, 3.26%.

후처리

  1. temperaturewas heated
  2. temperatureto reflux for 2 h (TLC monitored)
  3. customThe organic layer was separated
  4. washwashed with brine (20 mL)
  5. dry with materialdried over sodium sulphate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by column chromatography (EtOAc:hexane, 1:25, Rf: 0.28)

출처 및 근거

ORD 기록
ord-fcb20ac347e042dcb5f0de838d995e0f
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07745472B2

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