Hydrogen Bromide → p-Xylyl bromide

HRID 849707Notes

Reaction equation

HRID 849707 reaction equation
[C:1]1([CH3:7])[CH:6]=CC=[CH:3][CH:2]=1.[BrH:8].O1[CH2:14][CH2:13][CH2:12]OO1>[Br-].C([N+](CC)(CC)CC)C1C=CC=CC=1.C(O)(=O)C>[Br:8][CH2:12][C:13]1[CH:14]=[CH:6][C:1]([CH3:7])=[CH:2][CH:3]=1

Participants

6

Reactant 3

HCID 260Hydrogen BromideHCID 1140TolueneHCID 19593658CID 19593658

Product 1

HCID 7721p-Xylyl bromide

Reagents, catalysts & solvents 2

HCID 165294Benzyltriethylammonium bromideCatalystHCID 176Acetic AcidSolvent

Conditions

Temperature
70 °C

Procedure

Toluene (18 g) was added to a mixture of acetic acid (25 ml) and hydrobromic acid (95 ml), followed by trioxane (6.6 g) and benzyltriethylammonium bromide (2.0 g). The mixture was then heated to 70° C. and stirred well at the same temperature for 20 hours. After cooling to room temperature, the mixture was extracted with dichloromethane and then concentrated to give oil residue. The oil residue was distilled under vacuum to give the target product, 4-bromomethyltoluene (30.0 g). Result of measurement by NMR(CDCl3, ppm) was 2.4(3H, s), 4.5(2H, s), 7.3(4H, dd).

Workup

  1. temperatureAfter cooling to room temperature
  2. extractionthe mixture was extracted with dichloromethane
  3. concentrationconcentrated
  4. customto give oil residue
  5. distillationThe oil residue was distilled under vacuum

Sources & evidence

ORD record
ord-4742907695414a40b75ee505749524f6
Source dataset
uspto-grants-2000_01
Patent number
US06013832

Reaction notes

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