Carbon tetrabromide → Ethyl 2-(4-bromomethylphenoxy)-2-(3,4-methylenedioxyphenyl)acetate

HRID 274944Notes

Reaction equation

HRID 274944 reaction equation
[C:1]([CH:4]([C:23]1[CH:28]=[CH:27][C:26]2[O:29][CH2:30][O:31][C:25]=2[CH:24]=1)[O:5][C:6]1[CH:11]=[CH:10][C:9]([CH2:12]N2C3C=CC=CC=3NC2=O)=[CH:8][CH:7]=1)([OH:3])=[O:2].C1(P([C:45]2[CH:50]=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(Br)(Br)(Br)[Br:52].CCOC(C)=O.CCCCCC>ClCCl>[Br:52][CH2:12][C:9]1[CH:10]=[CH:11][C:6]([O:5][CH:4]([C:23]2[CH:28]=[CH:27][C:26]3[O:29][CH2:30][O:31][C:25]=3[CH:24]=2)[C:1]([O:3][CH2:50][CH3:45])=[O:2])=[CH:7][CH:8]=1

Participants

6

Reactant 4

HCID 11205Carbon tetrabromide2×HCID 11776Triphenylphosphine2×HCID 152317851-[4-(1-Carboxy-1-(3,4-methylenedioxyphenyl)methoxy)phenylmethyl]-2-benzimidazolinoneHCID 21226206Ethyl acetate hexane

Product 1

HCID 20089188Ethyl 2-(4-bromomethylphenoxy)-2-(3,4-methylenedioxyphenyl)acetateYield 109.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a cooled (0°-5° C.), magnetically stirred solution of 0.238 g (0.63 mmol) of the product of step A and 0.197 g (0.75 mmol) of triphenylphosphine dissolved in 3 mL of dichloromethane was added 0.287 g (0.75 mmol) of carbon tetrabromide in several portions. After the addition was complete, the reaction was allowed to warm to room temperature and was stirred 2.5 hours. At this point TLC analysis (50% EtOAc-hexane) indicated that starting material remained, therefore an additional 0.030 g of triphenylphosphine and 0.050 g of carbon tetrabromide were added. After 4 hours, the methylene chloride was 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 0.271 g (96%) of the title compound.

Workup

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

Sources & evidence

ORD record
ord-d89393715fa14b4197c368f71df6d08a
Source dataset
uspto-grants-1995_02
Patent number
US05391566

Reaction notes

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