Carbon tetrabromide → Methyl 2-(4-bromomethyl-2,6-dichlorophenoxy)-2-phenylacetate

HRID 2255605Notes

Reaction equation

HRID 2255605 reaction equation
[Cl:1][C:2]1[CH:19]=[C:18]([CH2:20]O)[CH:17]=[C:16]([Cl:22])[C:3]=1[O:4][CH:5]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[C:6]([O:8][CH3:9])=[O:7].C(Br)(Br)(Br)[Br:24].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C(Cl)Cl>[Br:24][CH2:20][C:18]1[CH:19]=[C:2]([Cl:1])[C:3]([O:4][CH:5]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[C:6]([O:8][CH3:9])=[O:7])=[C:16]([Cl:22])[CH:17]=1

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 19385731Methyl 2-(2,6-dichloro-4-hydroxymethylphenoxy)-2-phenylacetate

Product 1

HCID 19385677Methyl 2-(4-bromomethyl-2,6-dichlorophenoxy)-2-phenylacetateYield 78.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred and cooled (0° C.) solution of 0.140 g (0.41 mmol) of the product of Step D dissolved in 2 mL of CH2Cl2 was added 0.170 g (0.51 mmol) of carbon tetrabromide and 0.135 g (0.51 mmol) of triphenylphosphine. After the addition the reaction mixture was allowed to warm to room temperature and was stirred overnight. The mixture was then evaporated in vacuo and purified on a silica gel flash chromatography column eluted with 15% ethyl acetate/hexane to afford 0.130 g (78%) of the title compound.

Workup

  1. additionAfter the addition the reaction mixture
  2. stirringwas stirred overnight
  3. customThe mixture was then evaporated in vacuo
  4. custompurified on a silica gel flash chromatography column
  5. washeluted with 15% ethyl acetate/hexane

Sources & evidence

ORD record
ord-4fd95984322345d09124ae858cdb5c84
Source dataset
uspto-grants-1993_08
Patent number
US05240938

Reaction notes

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