Cesium carbonate → HCID 57608491, compound

HRID 1399945Notes

Reaction equation

HRID 1399945 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([SH:8])[CH:5]=[CH:6][CH:7]=1.Br[CH2:10][CH2:11][OH:12].C([O-])([O-])=O.[Cs+].[Cs+]>CN(C=O)C.C(OCC)(=O)C>[Br:1][C:2]1[CH:3]=[C:4]([S:8][CH2:10][CH2:11][OH:12])[CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 108982-BromoethanolHCID 80597m-Bromobenzenethiol

Product 1

HCID 57608491HCID 57608491, compoundYield 81.1%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of 3-bromobenzenethiol (1.5 g, 7.93 mmol), 2-bromoethanol (1.19 g, 9.52 mmol) and Cs2CO3 (5.16 g, 15.8 mmol) in DMF (10 ml) was heated to 50° C. overnight. The reaction mixture was diluted with ethyl acetate and filtered. The filtrate was washed with water and dried. The crude product was purified by column chromatography to afford the titled compound (1.5 g, 81%). 1HNMR (400 MHz, CDCl3): δ 3.12 (t, J=6.0 Hz, 2H), 3.77 (t, J=6.4 Hz, 2H), 7.14 (t, J=8.0 Hz, 1H), 7.26-7.34 (m, 2H), 7.51 (s, 1H).

Workup

  1. filtrationfiltered
  2. washThe filtrate was washed with water
  3. customdried
  4. customThe crude product was purified by column chromatography

Sources & evidence

ORD record
ord-cbcc721758294af1bd56c5b9d993515a
Source dataset
uspto-grants-2014_12
Patent number
US08906909B2

Reaction notes

Loading…