Cesium carbonate → HCID 59235327, compound

HRID 2174340Notes

Reaction equation

HRID 2174340 reaction equation
CC1C=CC(S(O[CH2:12][CH2:13][O:14][CH2:15][CH:16]([F:18])[F:17])(=O)=O)=CC=1.[Br:19][C:20]1[CH:21]=[CH:22][C:23]([Cl:34])=[C:24]([CH:33]=1)[CH2:25][C:26]1[CH:31]=[CH:30][C:29]([OH:32])=[CH:28][CH:27]=1.C([O-])([O-])=O.[Cs+].[Cs+]>CN(C=O)C.O>[Br:19][C:20]1[CH:21]=[CH:22][C:23]([Cl:34])=[C:24]([CH2:25][C:26]2[CH:31]=[CH:30][C:29]([O:32][CH2:12][CH2:13][O:14][CH2:15][CH:16]([F:18])[F:17])=[CH:28][CH:27]=2)[CH:33]=1

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 574237514-((5-Bromo-2-chlorophenyl)methyl)phenolHCID 59557759HCID 59557759, compound

Product 1

HCID 59235327HCID 59235327, compoundYield 92.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

2-(2,2-difluoroethoxy)ethyl 4-methylbenzenesulfonate (3 g, 10.7 mmol), 4-(5-bromo-2-chlorobenzyl)phenol (3.8 g, 12.8 mmol), and Cs2CO3 (8.7 g, 26.8 mmol) were suspended in DMF (8 mL) at 50° C. The mixture was stirred for 24 hours at this temperature. The mixture was diluted with water and the aqueous layer was extracted with PE two times. The combined organic layers were washed with brine, concentrated and purified by flash chromatography (PE/EtOAc=50:1) to obtain a yellow solid (4 g, yield 91.9%), which was used in the next step without further purification.

Workup

  1. extractionthe aqueous layer was extracted with PE two times
  2. washThe combined organic layers were washed with brine
  3. concentrationconcentrated
  4. custompurified by flash chromatography (PE/EtOAc=50:1)

Sources & evidence

ORD record
ord-33fa1b2107c648938470cae4a78c7596
Source dataset
uspto-grants-2015_06
Patent number
US09061060B2

Reaction notes

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