Carbon tetrabromide → Methyl 2-(4-bromomethyl-2-chloro-6-propylphenoxy)-2-(3,4-methylenedioxyphenyl)acetate

HRID 274933Notes

Reaction equation

HRID 274933 reaction equation
[Cl:1][C:2]1[CH:22]=[C:21]([CH2:23]O)[CH:20]=[C:19]([CH2:25][CH2:26][CH3:27])[C:3]=1[O:4][CH:5]([C:10]1[CH:15]=[CH:14][C:13]2[O:16][CH2:17][O:18][C:12]=2[CH:11]=1)[C:6]([O:8][CH3:9])=[O:7].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(Br)(Br)(Br)[Br:48]>ClCCl>[Br:48][CH2:23][C:21]1[CH:20]=[C:19]([CH2:25][CH2:26][CH3:27])[C:3]([O:4][CH:5]([C:10]2[CH:15]=[CH:14][C:13]3[O:16][CH2:17][O:18][C:12]=3[CH:11]=2)[C:6]([O:8][CH3:9])=[O:7])=[C:2]([Cl:1])[CH:22]=1

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 20089199Methyl 2-(2-chloro-4-hydroxymethyl-6-propylphenoxy)-2-(3,4-methylenedioxyphenyl)acetate

Product 1

HCID 20089193Methyl 2-(4-bromomethyl-2-chloro-6-propylphenoxy)-2-(3,4-methylenedioxyphenyl)acetate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a cooled (0°-5° C.), magnetically stirred solution of 0.445 g (1.13 mmol) of the product of step D and 0.446 g (1.70 mmol) of triphenylphosphine dissolved in 5 mL of dichloromethane was added 0.564 g (1.70 mmol) of carbon tetrabromide in several portions. After the addition was complete, the reaction was allowed to warm to room temperature and was stirred an additional 30 minutes. The methylene chloride was then removed in vacuo, and the residue was applied to a silica gel flash chromatography column and eluted with 10% EtOAc-hexane. Evaporation of the purified fractions and drying in vacuo afforded the title compound which was used directly in the next step without further characterization.

Workup

  1. additionAfter the addition
  2. customThe methylene chloride was then removed in vacuo
  3. washeluted with 10% EtOAc-hexane
  4. customEvaporation of the purified fractions
  5. customdrying in vacuo

Sources & evidence

ORD record
ord-07a030bf6b6d4bf986eb2ebb1d9d3b8f
Source dataset
uspto-grants-1995_02
Patent number
US05391566

Reaction notes

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