1-Bromo-3-chloropropane → HCID 66649121, compound

HRID 2193768Notes

Reaction equation

HRID 2193768 reaction equation
[F:1][C:2]1[CH:25]=[C:24]([N+:26]([O-:28])=[O:27])[CH:23]=[CH:22][C:3]=1[O:4][C:5]1[CH:10]=[CH:9][N:8]=[C:7]2[CH:11]=[C:12]([C:14]3[CH:15]=[C:16]([OH:21])[C:17]([OH:20])=[CH:18][CH:19]=3)[S:13][C:6]=12.Br[CH2:30][CH2:31][CH2:32][Cl:33].C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C.CCOC(C)=O>[Cl:33][CH2:32][CH2:31][CH2:30][O:21][C:16]1[CH:15]=[C:14]([C:12]2[S:13][C:6]3[C:7](=[N:8][CH:9]=[CH:10][C:5]=3[O:4][C:3]3[CH:22]=[CH:23][C:24]([N+:26]([O-:28])=[O:27])=[CH:25][C:2]=3[F:1])[CH:11]=2)[CH:19]=[CH:18][C:17]=1[O:20][CH2:30][CH2:31][CH2:32][Cl:33]

Participants

6

Reactant 3

HCID 80061-Bromo-3-chloropropaneHCID 10796Cesium carbonateHCID 136342633HCID 136342633, compound

Product 1

HCID 66649121HCID 66649121, compoundYield 62.2%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of 332 (140 mg, 0.35 mmol) in anhydrous DMF (5 ml) were added 1-bromo-3-chloropropane (553 mg, 3.51 mmol) and cesium carbonate (573 mg, 1.76 mmol), respectively. The reaction mixture was stirred for 2 hrs at room temperature, diluted with AcOEt, and successively washed with water, sat. ammonium chloride, water, and concentrated. The crude material was adsorbed on silica gel and purified by flash column chromatography (eluents AcOEt/CH2Cl2: 10/90 to 20/80) to afford title compound 333 (120 mg, 62% yield) as a yellow solid. MS (m/z): 551.0 and 553.0 (M+H)+.

Workup

  1. washsuccessively washed with water, sat. ammonium chloride, water
  2. concentrationconcentrated
  3. custompurified by flash column chromatography (eluents AcOEt/CH2Cl2: 10/90 to 20/80)

Sources & evidence

ORD record
ord-d9a953eeacd1431aa94931aea3357edd
Source dataset
uspto-grants-2012_12
Patent number
US08329726B2

Reaction notes

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