Water → 3-Benzoyloxy-4-chlorobenzyl bromide

HRID 19923

반응식

HRID 19923 반응식
[Cl: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]([Cl: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 167492223-Benzoyloxy-4-chlorotoluene

생성물 1

HCID 167478403-Benzoyloxy-4-chlorobenzyl bromide

시약·촉매·용매 2

HCID 3283Diethyl Ether용매HCID 5943Carbon Tetrachloride용매

실험 절차

A mixture of benzoic acid 2-chloro-5-methyl-phenyl ester (CAB02124, 2.47 g, 10.0 mmol), N-bromo-succinimide (1.96 g, 11.0 mmol) and dibenzoyl peroxide (10 mg) in carbon tetrachloride (25 mL) was heated to reflux for 1 hour (TLC-control). 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, 1:40, Rf: 0.21). Yield: 2.012 g (62%) colourless oil, which solidified after a few hours (contains ca. 10% benzoic acid 5-dibromomethyl-2-chloro-phenyl ester).

후처리

  1. temperaturewas heated
  2. temperatureto reflux for 1 hour (TLC-control)
  3. additionwere added
  4. customThe organic layer was separated
  5. washwashed with brine (20 mL)
  6. dry with materialdried over sodium sulphate
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by column chromatography (EtOAc:hexane, 1:40, Rf: 0.21)
  9. waitYield: 2.012 g (62%) colourless oil, which solidified after a few hours

출처 및 근거

ORD 기록
ord-cf649b7a6cbf4902bba31782f4cdf429
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07745472B2

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