Benzene, 1-bromo-3-iodo- → Ethyl 3-[(3-bromophenyl)thio]propanoate

HRID 1593030Notes

Reaction equation

HRID 1593030 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4](I)[CH:3]=1.[SH:9][CH2:10][CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13]>CN(C)C=O.C(N(CC)CC)C.C(OCC)(=O)C.C1(P(C2C=CC=CC=2)[C-]2C=CC=C2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2].C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[Br:1][C:2]1[CH:3]=[C:4]([S:9][CH2:10][CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH:5]=[CH:6][CH:7]=1

Participants

8

Reactant 2

HCID 11561Benzene, 1-bromo-3-iodo-HCID 21625Ethyl 3-mercaptopropionate

Product 1

HCID 62805311Ethyl 3-[(3-bromophenyl)thio]propanoate

Reagents, catalysts & solvents 5

HCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)CatalystHCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 6228DimethylformamideSolventHCID 8471TriethylamineSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 1-bromo-3-iodobenzene (3 g) and 1,1′-bis(diphenylphosphino)ferrocene (90 mg) in dimethylformamide (10 ml) and triethylamine (2 ml) was treated with tris(dibenzylideneacetone)dipalladium (175 mg) at 20° C. under nitrogen. After 10 min ethyl 3-mercaptopropionate (1.14 ml) was added and the mixture was heated to 60° C. for 1.5 h. The mixture was diluted with ethyl acetate and washed with 2M hydrochloric acid, brine and dried (MgSO4). The filtrate was concentrated and chromatographed on a biotage cartridge (40 g) eluting with dichloromethane-cyclohexane (1:3) to give the title compound (1.58 g) LCMS RT=3.50 min

Workup

  1. washwashed with 2M hydrochloric acid, brine
  2. dry with materialdried (MgSO4)
  3. concentrationThe filtrate was concentrated
  4. customchromatographed on a biotage cartridge (40 g)
  5. washeluting with dichloromethane-cyclohexane (1:3)

Sources & evidence

ORD record
ord-1447a8735663439383d853df2a84b6c9
Source dataset
uspto-grants-2007_11
Patent number
US07294650B2

Reaction notes

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