Carbon Tetrachloride → 3-Chloro-5-methoxybenzyl bromide

HRID 83856

반응식

HRID 83856 반응식
Cl[C:2]1C=[CH:6][C:5]([CH3:8])=[CH:4][C:3]=1[O:9][CH3:10].C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1.C1C(=O)N([Br:36])C(=O)C1.[C:37]([Cl:41])(Cl)(Cl)Cl>>[Br:36][CH2:8][C:5]1[CH:6]=[C:37]([Cl:41])[CH:2]=[C:3]([O:9][CH3:10])[CH:4]=1

참가 물질

5

반응물 4

HCID 5943Carbon TetrachlorideHCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 993521-Chloro-2-methoxy-4-methylbenzene

생성물 1

HCID 534030783-Chloro-5-methoxybenzyl bromide

실험 절차

To a solution of 2-chloro-5-methylanisole (11) (274 g, 1.75 mol) in CCl4 (2.5 L) was added benzoyl peroxide (4.23 g, 0.02 mol) and NBS (321 g, 1.80 mol). The reaction mixture was heated to reflux for 1 h with mechanical stirring. The reaction mixture was cooled, washed with 1N HCl (2 L), satd NaHCO3 (2 L) and brine (2 L), dried over MgSO4, filtered and concentrated under reduced pressure to give the 5-(bromomethyl)-3-chloroanisole (12) as a light yellow solid (412 g, quantitative). 1H NMR (400 MHz, CDCl3): δ 7.30-7.34 (d, 1H), 6.95 (s, 1H), 6.91-6.93 (d, 1H), 4.45 (s, 2H), 3.92 (s, 3H).

후처리

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for 1 h with mechanical stirring
  3. temperatureThe reaction mixture was cooled
  4. washwashed with 1N HCl (2 L), satd NaHCO3 (2 L) and brine (2 L)
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-8943921278eb476893aaac11a751fff2
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08846739B2

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