Cesium carbonate → HCID 67513955, compound

HRID 1519641Notes

Reaction equation

HRID 1519641 reaction equation
[Br:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[C:4]([OH:10])[CH:3]=1.Br[CH:12]1[CH2:14][CH2:13]1.C([O-])([O-])=O.[Cs+].[Cs+]>CN(C=O)C>[Br:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[C:4]([O:10][CH:12]2[CH2:14][CH2:13]2)[CH:3]=1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 78037BromocyclopropaneHCID 129669614-Bromo-2-hydroxybenzonitrile

Product 1

HCID 67513955HCID 67513955, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
170 °C

Procedure

A mixture of 4-bromo-2-hydroxybenzonitrile (300 mg, 1.5 mmol), bromo-cyclopropane (480 mg, 4.0 mmol) and Cs2CO3 (300 mg, 1.6 mmol) in 2 mL of anhydrous DMF were heated to 170° C. for 2 hours by microwave. The solid was filtered off, and the filtrate was poured to water, and extracted with EtOAc. The organic layer was washed with brine, dried over sodium sulfate and concentrated. The residue was purified with prep-TLC to give 4-bromo-2-(cyclopropyloxy)benzonitrile. 1H-NMR (400 MHz, CDCl3) δ ppm 7.46˜7.48 (m, 1H), 7.36˜7.38 (m, 1H), 7.14˜7.16 (m, 1H), 3.79˜3.84 (m, 1H), 0.86˜0.87 (m, 4H).

Workup

  1. filtrationThe solid was filtered off
  2. additionthe filtrate was poured to water
  3. extractionextracted with EtOAc
  4. washThe organic layer was washed with brine
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated
  7. customThe residue was purified with prep-TLC

Sources & evidence

ORD record
ord-70232bfdbbce4f89bb8b7d2e62a7e42f
Source dataset
uspto-grants-2015_07
Patent number
US09073882B2

Reaction notes

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