3,4-Dichlorophenol → HCID 67079669, compound

HRID 655514Notes

Reaction equation

HRID 655514 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([OH:9])[CH:5]=[CH:6][C:7]=1[Cl:8].[C:10](N1C=CN=C1)([N:12]1[CH:16]=[CH:15][N:14]=[CH:13]1)=[O:11]>ClCCl>[Cl:1][C:2]1[CH:3]=[C:4]([O:9][C:10]([N:12]2[CH:16]=[CH:15][N:14]=[CH:13]2)=[O:11])[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

4

Reactant 2

HCID 72583,4-DichlorophenolHCID 682631,1'-Carbonyldiimidazole

Product 1

HCID 67079669HCID 67079669, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 5.00 g (30.7 mmol) of 3,4-dichlorophenol in 160 ml of dichloromethane was treated with 6.47 g (39.9 mmol) of 1,1′-carbonyldiimidazol. The reaction was stirred at room temperature over 3.5 h, then partitioned between aq. 0.5 M citric acid and dichloromethane (3×). The organic phase was dried over Na2SO4 evaporated and crystallized from diethyl ether to yield 5.03 g (64%) of the title compound as white crystals. MS: 256.8 (MH+, 2Cl).

Workup

  1. custompartitioned between aq. 0.5 M citric acid and dichloromethane (3×)
  2. dry with materialThe organic phase was dried over Na2SO4
  3. customevaporated
  4. customcrystallized from diethyl ether

Sources & evidence

ORD record
ord-4ee42af35f3c49c9a9938a42cdd14dc4
Source dataset
uspto-grants-2011_12
Patent number
US08071586B2

Reaction notes

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