2,4-Dichlorophenol → HCID 86746556, compound

HRID 2082129Notes

Reaction equation

HRID 2082129 reaction equation
[Br:1][CH2:2][C:3]1[CH:13]=[CH:12][C:6]([O:7]CC(O)=O)=[CH:5][CH:4]=1.[Cl:14][C:15]1[CH:20]=[C:19]([Cl:21])[CH:18]=[CH:17][C:16]=1O.C1(N=C=NC2CCCCC2)CCCCC1.[C:38]([O:41]CC)(=[O:40])[CH3:39]>>[C:38]([O:41][O:7][C:6]1[CH:5]=[CH:4][C:3]([CH2:2][Br:1])=[CH:13][C:12]=1[C:18]1[CH:17]=[CH:16][C:15]([Cl:14])=[CH:20][C:19]=1[Cl:21])(=[O:40])[CH3:39]

Participants

5

Reactant 4

HCID 84492,4-DichlorophenolHCID 8857Ethyl Acetate2×HCID 10868DicyclohexylcarbodiimideHCID 70106744-(BROMOMETHYL)PHENOXYACETIC ACID

Product 1

HCID 86746556HCID 86746556, compoundYield 85%

Procedure

To 4-bromomethylphenoxyacetic acid (20 g, 81.6 mole) and 2,4-dichlorophenol (14 g, 85.7 mole) suspended in 100 ml ethyl acetate at 0° C. was added solid dicyclohexylcarbodiimide (17.7 g, 85.8 mole) in portions with stirring. After two hours at 0° C., 200 ml of ethyl acetate was added to the thick suspension that resulted, and stirring was allowed to proceed for 30 minutes as the mixture was allowed to warm to room temperature. Insoluble dicyclohexylurea was removed by filtration and was washed with ethyl acetate (3×30 ml). The combined filtrate and washes were concentrated in vacuo and the residue was dissolved in 35 ml boiling ethyl acetate. Upon cooling to room temperature, crystalline product had formed. After addition of 155 ml hexanes in portions with mixing, the product was collected by vacuum filtration, washed with hexanes/ethyl acetate (9:1), and dried in vacuo to yield 26.8 g (85%) of crystalline product (mp 114°-6° C.). The product was homogeneous by TLC (silica gel 60) and had an Rf =0.50 when developed with hexanes:ethyl acetate (8:2).

Workup

  1. customthat resulted
  2. stirringstirring
  3. waitto proceed for 30 minutes as the mixture
  4. customInsoluble dicyclohexylurea was removed by filtration
  5. washwas washed with ethyl acetate (3×30 ml)
  6. concentrationThe combined filtrate and washes were concentrated in vacuo
  7. dissolutionthe residue was dissolved in 35 ml
  8. temperatureUpon cooling to room temperature
  9. customcrystalline product had formed
  10. additionwith mixing
  11. filtrationthe product was collected by vacuum filtration
  12. washwashed with hexanes/ethyl acetate (9:1)
  13. customdried in vacuo

Sources & evidence

ORD record
ord-a972e2e539f24a1d9e5888013f67d1f1
Source dataset
uspto-grants-1993_02
Patent number
US05187270

Reaction notes

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