Water → 6-Cyanoindane-4-carboxylic acid

HRID 749477Notes

Reaction equation

HRID 749477 reaction equation
Br[C:2]1[CH:3]=[C:4]([C:11]#[N:12])[CH:5]=[C:6]2[C:10]=1[CH2:9][CH2:8][CH2:7]2.CN([CH:16]=[O:17])C.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(N(CC)CC)C.[OH2:44]>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.CCOCC>[C:11]([C:4]1[CH:3]=[C:2]([C:16]([OH:17])=[O:44])[C:10]2[CH2:9][CH2:8][CH2:7][C:6]=2[CH:5]=1)#[N:12]

Participants

8

Reactant 5

HCID 962Water2×HCID 6228DimethylformamideHCID 8471TriethylamineHCID 11776TriphenylphosphineHCID 689791847-Bromoindane-5-carbonitrile

Product 1

HCID 689791816-Cyanoindane-4-carboxylic acidYield 60%

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 3283Diethyl EtherSolvent

Conditions

Temperature
90 °C

Procedure

In a flask designed for high pressure (max. 12 bar) 7-bromoindane-5-carbonitrile (1.18 g, 5.3 mmol) was mixed with DMF (50 mL), bis(triphenylphosphine)palladium(II) chloride (0.1 g, 0.14 mmol), triphenylphosphine (0.1 g, 0.38 mmol), triethylamine (1.0 g, 9.9 mmol) and water (5 mL). While stirring the flask was alternately evacuated and then loaded with carbon monoxide. The procedure was repeated 4 times and then carbon monoxide was introduced until a pressure of 6 bar was obtained. The reaction mixture was heated to 90° C. for 60 h and then cooled to room temperature. The content was transferred to a beaker by means of ether (100 mL) and water (200 mL). The organic layer was separated off and precipitated Pd was removed by decantation. The aqueous layer was acidified with conc. HCl and then extracted thrice with ether (50 mL). The combined organic solutions were washed with brine, dried over Na2SO4 and the solvent was evaporated. The solid residue was treated with cold CH2Cl2, then filtrated off and then dried. There was obtained 0.6 g (60%) of 6-cyanoindane-4-carboxylic acid as a solid material. 1H NMR (300 MHz, CDCl3): 2.1-2.2 (q, 2H), 3.0 (t, 2H), 3.4 (t, 2H), 7.7 (s, 1H), 8.2 (s, 1H).

Workup

  1. customwas alternately evacuated
  2. additioncarbon monoxide was introduced until a pressure of 6 bar
  3. customwas obtained
  4. temperaturecooled to room temperature
  5. customThe organic layer was separated off
  6. customprecipitated Pd
  7. customwas removed by decantation
  8. extractionextracted thrice with ether (50 mL)
  9. washThe combined organic solutions were washed with brine
  10. dry with materialdried over Na2SO4
  11. customthe solvent was evaporated
  12. additionThe solid residue was treated with cold CH2Cl2
  13. filtrationfiltrated off
  14. customdried

Sources & evidence

ORD record
ord-04ec927cf1a24760a7ef8da6b4e62327
Source dataset
uspto-grants-2008_07
Patent number
US07402581B2

Reaction notes

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