Carbon Tetrachloride → 3-Chloro-5-methoxybenzyl bromide

HRID 1627341Notes

Reaction equation

HRID 1627341 reaction equation
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

Participants

5

Reactant 4

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

Product 1

HCID 534030783-Chloro-5-methoxybenzyl bromide

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-eaebf32f2be44d67bf7df7fe4aae6e62
Source dataset
uspto-grants-2014_07
Patent number
US08785488B2

Reaction notes

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