Cesium carbonate → [4-Chloro-3-(3-cyanophenoxy)phenyl]acetic acid

HRID 1686386Notes

Reaction equation

HRID 1686386 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([OH:11])=[O:10])=[CH:4][C:3]=1[OH:12].Br[C:14]1[CH:15]=[C:16]([CH:19]=[CH:20][CH:21]=1)[C:17]#[N:18].C(=O)([O-])[O-].[Cs+].[Cs+].CC(C)(C(=O)CC(=O)C(C)(C)C)C>[Cu]Cl.CN1C(=O)CCC1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([OH:11])=[O:10])=[CH:4][C:3]=1[O:12][C:14]1[CH:21]=[CH:20][CH:19]=[C:16]([C:17]#[N:18])[CH:15]=1

Participants

7

Reactant 4

HCID 10796Cesium carbonateHCID 233813-BromobenzonitrileHCID 707002,2,6,6-Tetramethyl-3,5-heptanedioneHCID 30171834-Chloro-3-hydroxyphenylacetic acid

Product 1

HCID 57791937[4-Chloro-3-(3-cyanophenoxy)phenyl]acetic acidYield 1.9%

Reagents, catalysts & solvents 2

HCID 62652Cuprous chlorideCatalystHCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
120 °C

Procedure

The product from example 1 step (iii) (0.5 g), 3-bromobenzonitrile (0.73 g), cesium carbonate (2.61 g), copper(I) chloride (0.13 g), 2,2,6,6-tetramethyl-3,5-heptanedione (0.06 ml) and NMP (10 ml) were charged to a flask and heated at 120° C. for 16 h. The mixture was partitioned between ether and 2M NaOH, the aqueous layer was acidified then extracted with EtOAc, dried (MgSO4) and evaporated under reduced pressure. The residue was purified by RPHPLC to give the title compound (0.015 g).

Workup

  1. customThe mixture was partitioned between ether and 2M NaOH
  2. extractionthe aqueous layer was acidified then extracted with EtOAc
  3. dry with materialdried (MgSO4)
  4. customevaporated under reduced pressure
  5. customThe residue was purified by RPHPLC

Sources & evidence

ORD record
ord-70c78f77bbb74a479398e9b55a6403ac
Source dataset
uspto-grants-2012_04
Patent number
US08148572B2

Reaction notes

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