Carbon tetrabromide → Methyl 2-(4-bromomethylphenoxy)-3-phenylpropanoate

HRID 2399503Notes

Reaction equation

HRID 2399503 reaction equation
O[CH2:2][C:3]1[CH:21]=[CH:20][C:6]([O:7][CH:8]([CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:9]([O:11][CH3:12])=[O:10])=[CH:5][CH:4]=1.C(Br)(Br)(Br)[Br:23].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C(Cl)Cl>[Br:23][CH2:2][C:3]1[CH:21]=[CH:20][C:6]([O:7][CH:8]([CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:9]([O:11][CH3:12])=[O:10])=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 19385635Methyl 2-(4-hydroxymethylphenoxy)-3-phenylpropanoate

Product 1

HCID 19385585Methyl 2-(4-bromomethylphenoxy)-3-phenylpropanoateYield 35%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a cooled (0° C.) solution of 0.230 g (0.80 mmol) of the product of Step D dissolved in 4 mL of CH2Cl2 was added 0.263 g (1.00 mmol) of carbon tetrabromide and 0.333 g (1.00 mmol) of triphenylphosphine. After 15 minutes at 0° C., the reaction mixture was allowed to warm to room temperature and was stirred for an additional 6 hours. The reaction was then concentrated in vacuo and purified on a silica gel flash chromatography column eluted with 5% ethyl acetate/hexane to afford 097 g (35%) of the title compound.

Workup

  1. concentrationThe reaction was then concentrated in vacuo
  2. custompurified on a silica gel flash chromatography column
  3. washeluted with 5% ethyl acetate/hexane
  4. customto afford 097

Sources & evidence

ORD record
ord-ef63322e8dff423c9c73c928d28c6b46
Source dataset
uspto-grants-1995_09
Patent number
US05449682

Reaction notes

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