Boron tribromide → 2-Amino-4-(4-hydroxyphenyl)thiophene-3-carbonitrile

HRID 1518321Notes

Reaction equation

HRID 1518321 reaction equation
[NH2:1][C:2]1[S:3][CH:4]=[C:5]([C:9]2[CH:14]=[CH:13][C:12]([O:15]CC3C=CC=CC=3)=[CH:11][CH:10]=2)[C:6]=1[C:7]#[N:8].B(Br)(Br)Br>C(Cl)Cl>[NH2:1][C:2]1[S:3][CH:4]=[C:5]([C:9]2[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][CH:10]=2)[C:6]=1[C:7]#[N:8]

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 594474742-Amino-4-(4-(benzyloxy)phenyl)thiophene-3-carbonitrile

Product 1

HCID 152199602-Amino-4-(4-hydroxyphenyl)thiophene-3-carbonitrileYield 83.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To compound 47B (1.1 g, 3.59 mmol) in DCM (80 mL) was added 1.0 M BBr3 (36 mL, 36 mmol) in DCM at rt. A precipitate formed upon addition and gradually disappeared after stirring at rt for 2 hours. The solvent was removed, and the residue was partitioned between water and EtOAc. The organic layer was isolated. The aqueous layer was extracted with EtOAc. The combined organic layers were washed with brine, dried over MgSO4, filtered, and concentrated under reduced pressure. The crude material was purified by column chromatography on silica gel eluting with 3:2/hexanes:EtOAc to provide 0.65 g of the desired product 47C: 1H NMR (DMSO-d6): δ 9.58 (s, 1H), 7.35 (d, J=8.73 Hz, 2H), 7.15 (s, 2H), 6.80 (d, J=8.73 Hz, 2H), 6.34 (s, 1H); MS (ESI(+)): m/z 217 (M+H).

Workup

  1. customA precipitate formed upon addition
  2. customThe solvent was removed
  3. customthe residue was partitioned between water and EtOAc
  4. customThe organic layer was isolated
  5. extractionThe aqueous layer was extracted with EtOAc
  6. washThe combined organic layers were washed with brine
  7. dry with materialdried over MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure
  10. customThe crude material was purified by column chromatography on silica gel eluting with 3:2/hexanes

Sources & evidence

ORD record
ord-7ea1b03ea0ca47a9b7f28dbc7cbf787b
Source dataset
uspto-grants-2012_07
Patent number
US08232273B2

Reaction notes

Loading…