Boron tribromide → 4-(4,7-Dihydro-1-thia-4,5-diaza-cyclopenta[a]pentalen-6-yl)-phenol

HRID 532701Notes

Reaction equation

HRID 532701 reaction equation
B(Br)(Br)Br.C[O:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]2[C:17]3[CH2:18][C:19]4[S:20][CH:21]=[CH:22][C:23]=4[C:16]=3[NH:15][N:14]=2)=[CH:9][CH:8]=1>C(Cl)Cl>[S:20]1[CH:21]=[CH:22][C:23]2[C:16]3[NH:15][N:14]=[C:13]([C:10]4[CH:11]=[CH:12][C:7]([OH:6])=[CH:8][CH:9]=4)[C:17]=3[CH2:18][C:19]1=2

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 866992576-(4-Methoxy-phenyl)-4,7-dihydro-1-thia-4,5-diaza-cyclopenta[a]pentalene

Product 1

HCID 1362740514-(4,7-Dihydro-1-thia-4,5-diaza-cyclopenta[a]pentalen-6-yl)-phenolYield 88%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

BBr3 (1.25 g, 5.0 mmol) was added to a solution of 6-(4-Methoxy-phenyl)-4,7-dihydro-1-thia-4,5-diaza-cyclopenta[a]pentalene (0.13 g, 0.5 mmol) in CH2Cl2 (8.0 mL). After 2 hours, the solution was evaporated and washed with EtOAc, filtered, and concentrated to give the corresponding 4-(4,7-Dihydro-1-thia-4,5-diaza-cyclopenta[a]pentalen-6-yl)-phenol (0.11 g, 0.44 mmol) as brown solid in 88% yield.

Workup

  1. customthe solution was evaporated
  2. washwashed with EtOAc
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-14ab5a33d93346c995514b7f024930d1
Source dataset
uspto-grants-2014_10
Patent number
US08853207B2

Reaction notes

Loading…