Benzoyl Peroxide → 2-(Bromomethyl)anthracene

HRID 1729463노트

반응식

HRID 1729463 반응식
[CH3:1][C:2]1[CH:15]=[CH:14][C:13]2[C:4](=[CH:5][C:6]3[C:11]([CH:12]=2)=[CH:10][CH:9]=[CH:8][CH:7]=3)[CH:3]=1.[Br:16]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl>[Br:16][CH2:1][C:2]1[CH:15]=[CH:14][C:13]2[C:4](=[CH:5][C:6]3[C:11]([CH:12]=2)=[CH:10][CH:9]=[CH:8][CH:7]=3)[CH:3]=1

참가 물질

5

반응물 3

HCID 7187Benzoyl PeroxideHCID 119362-MethylanthraceneHCID 67184N-bromobutanimide

생성물 1

HCID 190129612-(Bromomethyl)anthracene수율 109.2%

시약·촉매·용매 1

HCID 5943Carbon Tetrachloride용매

실험 절차

2-Methylanthracene (5.00 g, 26.25 mmol, 1 eq), N-bromosuccinimide (4.70 g, 26.25 mmol, 1 eq), benzoyl peroxide (1.0 g) and carbon tetrachloride (250 mL) were mixed and refluxed for 6 hours. The mixture was cooled to room temperature, and the succinimide precipitate filtered. The filtrate was evaporated to dryness and the residue taken up in ethyl acetate (250 mL) and washed with 1 N NaOH (3×200 mL). The organic layer was dried (MgSO4) and the solvent removed in vacuo to yield 7.77 g of a light brown solid which was used without purification in the next step. NMR (DMSO-d6): δ 4.90 (s, 2H, CH2Br). ##STR55##

후처리

  1. temperaturerefluxed for 6 hours
  2. filtrationthe succinimide precipitate filtered
  3. customThe filtrate was evaporated to dryness
  4. washwashed with 1 N NaOH (3×200 mL)
  5. dry with materialThe organic layer was dried (MgSO4)
  6. customthe solvent removed in vacuo

출처 및 근거

ORD 기록
ord-28301d9a26ca4e53a6cc789a50c1282d
출처 데이터셋
uspto-grants-1994_07
특허 번호
US05332820

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