N-bromobutanimide → 3-(Bromomethyl)-2,4-dichloro-1,1'-biphenyl

HRID 1732637Notes

Reaction equation

HRID 1732637 reaction equation
[Cl:1][C:2]1[C:7]([CH3:8])=[C:6]([Cl:9])[CH:5]=[CH:4][C:3]=1[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.[Br:16]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl>[Br:16][CH2:8][C:7]1[C:2]([Cl:1])=[C:3]([C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH:4]=[CH:5][C:6]=1[Cl:9]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 20270616HCID 20270616, compound

Product 1

HCID 203043003-(Bromomethyl)-2,4-dichloro-1,1'-biphenylYield 99.1%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

A stirred solution of 10.6 g (0.045 mole) of 2,4-dichloro-3-methyl[1,1'-biphenyl] and 8.0 g (0.045 mole) of N-bromosuccinimide in 100 ml of carbon tetrachloride was irradiated with a 250 watt infra-red lamp for 4 hours. The reaction mixture was allowed to reflux from the heat of the lamp during the 4 hour period. The reaction mixture was filtered and the filter cake was washed with one portion of 100 ml of carbon tetrachloride. The wash and filtrate were combined and washed with one portion of a saturated aqueous solution of sodium chloride. The organic layer was dried with magnesium sulfate, filtered and the filtrate concentrated under reduced pressure to give 14.1 g of 3-bromomethyl-2,4-dichloro[1,1'-biphenyl]. The nmr spectrum was consistent with the proposed structure.

Workup

  1. temperatureto reflux from the
  2. temperatureheat of the lamp during the 4 hour period
  3. filtrationThe reaction mixture was filtered
  4. washthe filter cake was washed with one portion of 100 ml of carbon tetrachloride
  5. washThe wash
  6. washwashed with one portion of a saturated aqueous solution of sodium chloride
  7. dry with materialThe organic layer was dried with magnesium sulfate
  8. filtrationfiltered
  9. concentrationthe filtrate concentrated under reduced pressure

Sources & evidence

ORD record
ord-fc96b70dd73a409c820a14e71399a96f
Source dataset
uspto-grants-1980_12
Patent number
US04238505

Reaction notes

Loading…