Carbon Tetrachloride → 3-Chloro-5-methoxybenzyl bromide

HRID 83856

反応式

HRID 83856 の反応式
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

参加物

5

反応物 4

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

生成物 1

HCID 534030783-Chloro-5-methoxybenzyl bromide

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-8943921278eb476893aaac11a751fff2
出典データセット
uspto-grants-2014_09
特許番号
US08846739B2

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