Carbon tetrabromide → Ethyl 2-(4-bromomethyl-2,6-dichlorophenoxy)-2-(3,4-methylenedioxyphenyl)acetate

HRID 1741756Notes

Reaction equation

HRID 1741756 reaction equation
[Cl:1][C:2]1[CH:23]=[C:22]([CH2:24]O)[CH:21]=[C:20]([Cl:26])[C:3]=1[O:4][CH:5]([C:11]1[CH:16]=[CH:15][C:14]2[O:17][CH2:18][O:19][C:13]=2[CH:12]=1)[C:6]([O:8][CH2:9][CH3:10])=[O:7].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(Br)(Br)(Br)[Br:47]>C(Cl)Cl>[Br:47][CH2:24][C:22]1[CH:23]=[C:2]([Cl:1])[C:3]([O:4][CH:5]([C:11]2[CH:16]=[CH:15][C:14]3[O:17][CH2:18][O:19][C:13]=3[CH:12]=2)[C:6]([O:8][CH2:9][CH3:10])=[O:7])=[C:20]([Cl:26])[CH:21]=1

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 53743625Ethyl 2-(2,6-dichloro-4-hydroxymethylphenoxy)-2-(3,4-methylene dioxyphenyl)acetate

Product 1

HCID 20089189Ethyl 2-(4-bromomethyl-2,6-dichlorophenoxy)-2-(3,4-methylenedioxyphenyl)acetate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a magnetically stirred solution of 0.206 g (0.52 mmol) of the product of step A dissolved in 2 mL methylene chloride was added 0.162 g (0.62 mmol) of triphenylphosphine followed by 0.205 g (0.62 mmol) of carbon tetrabromide at 0° C. The reaction mixture was held at 0° C. for 10 minutes, then allowed to warm to room temperature and stirred for 2.5 hours. The reaction mixture was then concentrated in vacuo and the residue was applied to a silica gel flash chromatography column and eluted with 15% EtOAc-hexane. The purified fractions were combined, evaporated and dried in vacuo to afford 0.220 g (92%) yield of the title compound.

Workup

  1. concentrationThe reaction mixture was then concentrated in vacuo
  2. washeluted with 15% EtOAc-hexane
  3. customevaporated
  4. customdried in vacuo

Sources & evidence

ORD record
ord-4496569043534c9da08c124130586f70
Source dataset
uspto-grants-1994_08
Patent number
US05334598

Reaction notes

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