Benzene, 1,2-dichloro-3-methyl- → 1-(Bromomethyl)-2,3-dichlorobenzene

HRID 1706703Notes

Reaction equation

HRID 1706703 reaction equation
[Cl:1][C:2]1[C:7]([Cl:8])=[CH:6][CH:5]=[CH:4][C:3]=1[CH3:9].[Br:10]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl>[Br:10][CH2:9][C:3]1[CH:4]=[CH:5][CH:6]=[C:7]([Cl:8])[C:2]=1[Cl:1]

Participants

4

Reactant 2

HCID 34702Benzene, 1,2-dichloro-3-methyl-HCID 67184N-bromobutanimide

Product 1

HCID 27346021-(Bromomethyl)-2,3-dichlorobenzene

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

2,3-Dichlorotoluene (8.05 g., 0.05 mol.) dissolved in 150 ml. of carbon tetrachloride containing N-bromosuccinimide (8.9 g., 0.05 mol.) was heated to reflux and irradiated with a 275-watt sunlamp for two hours. The mixture was cooled, filtered and evaporated to give α-bromo-2,3-dichlorotoluene. The α-bromo-2,3-dichlorotoluene (2.4 g., 0.01 mol.) and thiourea (0.38 g., 0.005 mol.) were dissolved in 25 ml. of ethanol and refluxed for about sixteen hours. The mixture was cooled, concentrated, treated with ether, filtered and the filter cake recrystallized from water to give carbamimidothioic acid 2,3-dichlorobenzyl ester, m.p. 238°-243° C. (dec.).

Workup

  1. temperaturewas heated
  2. temperatureto reflux
  3. customirradiated with a 275-watt sunlamp for two hours
  4. temperatureThe mixture was cooled
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-8d36a50aafee4e3d91f0133f44d3a20b
Source dataset
uspto-grants-1980_06
Patent number
US04208430

Reaction notes

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