Dichloromethane → 7-Bromoindane-5-carboxamide

HRID 749475Notes

Reaction equation

HRID 749475 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:11]([OH:13])=O)[CH:5]=[C:6]2[C:10]=1[CH2:9][CH2:8][CH2:7]2.C(Cl)(=O)C(Cl)=O.C(Cl)Cl.[NH4+:23].[OH-]>C(O)C.CN(C=O)C>[Br:1][C:2]1[CH:3]=[C:4]([C:11]([NH2:23])=[O:13])[CH:5]=[C:6]2[C:10]=1[CH2:9][CH2:8][CH2:7]2

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 14923Ammonium HydroxideHCID 65578Oxalyl chlorideHCID 689774397-Bromoindane-5-carboxylic acid

Product 1

HCID 689803627-Bromoindane-5-carboxamideYield 68%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6228DimethylformamideSolvent

Procedure

7-Bromoindane-5-carboxylic acid (2.9 g, 12 mmol) and oxalylchloride (2.0 g, 16 mmol) were mixed with CH2Cl2 (50 mL) whereupon DMF (100 mg) was added. After 1 h at room temperature the mixture was poured into a mixture of concentrated NH4OH aq (20 mL) and ethanol (100 mL). The volatiles were removed by evaporation and the residue partitioned between ethyl acetate (100 mL) and water (50 mL). The organic layer was washed with brine and then dried over Na2SO4. The solvent was removed by evaporation and the solid residue was treated with cold CH2Cl2, then filtered off and dried. There was obtained 2.0 g (68%) of 7-bromoindane-5-carboxamide as a solid material. 1H NMR (300 MHz, CD3CO CD3): 2.0-2.2 (m, 2H), 2.8-2.9 (d, 2H), 2.9-3.0 (t, 1H), 3.0-3.1 (t, 1H), 6.5 (b, 1H), 7.4 (b, 1H), 7.7 (s, 1H), 7.9 (s,1H).

Workup

  1. additionwas added
  2. customThe volatiles were removed by evaporation
  3. customthe residue partitioned between ethyl acetate (100 mL) and water (50 mL)
  4. washThe organic layer was washed with brine
  5. dry with materialdried over Na2SO4
  6. customThe solvent was removed by evaporation
  7. additionthe solid residue was treated with cold CH2Cl2
  8. filtrationfiltered off
  9. customdried

Sources & evidence

ORD record
ord-5b885ecdd48e4a91ba47f81207948947
Source dataset
uspto-grants-2008_07
Patent number
US07402581B2

Reaction notes

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