Bromine → HCID 69513434, compound

HRID 1353197Notes

Reaction equation

HRID 1353197 reaction equation
[CH2:1]([O:3][C:4](=[O:17])[C@@H:5]([O:14][CH2:15][CH3:16])[CH2:6][C:7]1[CH:12]=[CH:11][C:10]([OH:13])=[CH:9][CH:8]=1)[CH3:2].[Br:18]Br>C(Cl)Cl>[CH2:1]([O:3][C:4](=[O:17])[C@@H:5]([O:14][CH2:15][CH3:16])[CH2:6][C:7]1[CH:8]=[CH:9][C:10]([OH:13])=[C:11]([Br:18])[CH:12]=1)[CH3:2]

Participants

4

Reactant 2

HCID 24408BromineHCID 9816147Ethyl (2S)-2-ethoxy-3-(4-hydroxyphenyl)propanoate

Product 1

HCID 69513434HCID 69513434, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a stirred solution of (S)-2-ethoxy-3-(4-hydroxyphenyl)-propionic acid ethyl ester (Tetrahedron Letters, Vol. 35, No 19, 3139–3142, 1994) (9.5 g, 40 mmol) in dry methylene chloride (100 ml) was over 1 h dropwise added a solution of bromine in methylene chloride (40 ml) at room temperature. The reaction was stirred for 60 min, washed with saturated sodium sulfite and brine. The organic phase was dried (MgSO4) and evaporated. The residue was purified by column chromatography using heptane:ethyl acetate (9:1) as eluent to give 11.25 g (88%) of (S)-3-(3-bromo-4-hydroxy-phenyl)-2-ethoxy-propionic acid ethyl ester.

Workup

  1. washwashed with saturated sodium sulfite and brine
  2. dry with materialThe organic phase was dried (MgSO4)
  3. customevaporated
  4. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-d3dabae805bd49ec8092aaa902d6c7de
Source dataset
uspto-grants-2007_05
Patent number
US07220877B2

Reaction notes

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