Dimethylformamide → Ethyl 3-(4-(3-iodobenzyloxy)phenyl)-3-(4-fluorophenyl)propanoate

HRID 1160314Notes

Reaction equation

HRID 1160314 reaction equation
C([O-])([O-])=O.[Cs+].[Cs+].Br[CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([I:15])[CH:10]=1.CN(C=O)C.[CH2:21]([O:23][C:24](=[O:41])[CH2:25][CH:26]([C:34]1[CH:39]=[CH:38][C:37]([F:40])=[CH:36][CH:35]=1)[C:27]1[CH:32]=[CH:31][C:30]([OH:33])=[CH:29][CH:28]=1)[CH3:22]>C(OCC)(=O)C>[I:15][C:11]1[CH:10]=[C:9]([CH:14]=[CH:13][CH:12]=1)[CH2:8][O:33][C:30]1[CH:31]=[CH:32][C:27]([CH:26]([C:34]2[CH:35]=[CH:36][C:37]([F:40])=[CH:38][CH:39]=2)[CH2:25][C:24]([O:23][CH2:21][CH3:22])=[O:41])=[CH:28][CH:29]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 10796Cesium carbonateHCID 27593613-Iodobenzyl bromideHCID 578357253-(4-Fluorophenyl)-3-(4-hydroxyphenyl)-propionic acid ethyl ester

Product 1

HCID 59132743Ethyl 3-(4-(3-iodobenzyloxy)phenyl)-3-(4-fluorophenyl)propanoate

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Cs2CO3 (4.89 g 15 mmol) and 1-(bromomethyl)-3-iodobenzene (4.45 g, 15 mmol) were added successively to a dry DMF (20 mL) solution of 45.2 (2.88 g, 10 mmol). The reaction mixture was stirred at room temperature overnight, diluted with ethyl acetate (200 mL), washed with water (100 mL×2) and brine (100 mL), and dried over Na2SO4. The solvent was removed under vacuum and the residue was purified by flash chromatography to give compound 47.1 as a colorless oil. MS ESI (pos.) m/e: 505.0 (1+H).

Workup

  1. washwashed with water (100 mL×2) and brine (100 mL)
  2. dry with materialdried over Na2SO4
  3. customThe solvent was removed under vacuum
  4. customthe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-a10a2b8da226401481ef7dfe131dfce7
Source dataset
uspto-grants-2010_10
Patent number
US07816367B2

Reaction notes

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