3,4-Dichlorophenol → HCID 86728173, compound

HRID 1848370Notes

Reaction equation

HRID 1848370 reaction equation
Br[CH2:2][CH2:3][CH2:4][NH:5][C:6](=[O:12])[O:7][C:8]([CH3:11])([CH3:10])[CH3:9].[Cl:13][C:14]1[CH:15]=[C:16]([OH:21])[CH:17]=[CH:18][C:19]=1[Cl:20].C([O-])([O-])=O.[Cs+].[Cs+]>CN(C=O)C.O>[Cl:13][C:14]1[CH:15]=[C:16]([CH:17]=[CH:18][C:19]=1[Cl:20])[O:21][CH2:2][CH2:3][CH2:4][NH:5][C:6](=[O:12])[O:7][C:8]([CH3:11])([CH3:10])[CH3:9]

Participants

6

Reactant 3

HCID 72583,4-DichlorophenolHCID 10796Cesium carbonateHCID 4460490tert-butyl N-(3-bromopropyl)carbamate

Product 1

HCID 86728173HCID 86728173, compoundYield 84.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of tert-butyl 3-bromopropylcarbamate (0.5 g, 2 mmol) and 3,4-dichlorophenol (0.38, 2.3 mmol) in DMF (10.5 mL) was added Cs2CO3 (1.02 g, 3.10 mmol). The reaction mixture was stirred at rt for 72 h. The reaction mixture was diluted with water and extracted with EtOAc (3×). The combined organic extracts were washed with saturated aqueous NaCl and water (1:1), dried over Na2SO4, filtered and evaporated to dryness. The crude product was purified by silica gel chromatography to provide Intermediate 3A (543 mg, 56% yield). HPLC/MS (Method B) RT=3.85 min, [M+H]+ 320.2.

Workup

  1. extractionextracted with EtOAc (3×)
  2. washThe combined organic extracts were washed with saturated aqueous NaCl and water (1:1)
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. customevaporated to dryness
  6. customThe crude product was purified by silica gel chromatography

Sources & evidence

ORD record
ord-38f24de0a01c46009711539946f3e130
Source dataset
uspto-grants-2015_02
Patent number
US08952180B2

Reaction notes

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