Boron tribromide → HCID 135776387, compound

HRID 2372366Notes

Reaction equation

HRID 2372366 reaction equation
B(Br)(Br)Br.C[O:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]2[N:14]=[N:15][S:16][C:17]=2[C:18]2[CH:23]=[CH:22][C:21]([O:24]C)=[CH:20][CH:19]=2)=[CH:9][CH:8]=1>C(Cl)Cl>[OH:6][C:7]1[CH:8]=[CH:9][C:10]([C:13]2[N:14]=[N:15][S:16][C:17]=2[C:18]2[CH:23]=[CH:22][C:21]([OH:24])=[CH:20][CH:19]=2)=[CH:11][CH:12]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 105181841,2,3-Thiadiazole, 4,5-bis(4-methoxyphenyl)-

Product 1

HCID 135776387HCID 135776387, compoundYield 77.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

Boron tribromide (102 ml of a 1 M solution in CH2Cl2) was added dropwise to a solution of thiadiazole 7 (8.0 g, 26.84 mmol) in CH2Cl2 (30 ml) at -78° C. After 2 hours the resulting dark green solution was warmed to 0° C. and quenched with 5% HCl. The aqueous layer was extracted twice with EtOAc. The organic layers were combined, dried over MgSO4, and the solvent was removed under reduced pressure. The crude yellow solid was dissolved in EtOAc and extracted twice with 5% NaOH. The aqueous layer was acidified with 10% HCl, and extracted twice with EtOAc. The organic layers were combined, dried over MgSO4, and the solvent was removed under reduced pressure. The resulting white solid was recrystallized from MeOH/H2O to afford 28 (5.58 g, 77.1%), m.p. 221.0°-222.0°60 C.

Workup

  1. customquenched with 5% HCl
  2. extractionThe aqueous layer was extracted twice with EtOAc
  3. dry with materialdried over MgSO4
  4. customthe solvent was removed under reduced pressure
  5. dissolutionThe crude yellow solid was dissolved in EtOAc
  6. extractionextracted twice with 5% NaOH
  7. extractionextracted twice with EtOAc
  8. dry with materialdried over MgSO4
  9. customthe solvent was removed under reduced pressure
  10. customThe resulting white solid was recrystallized from MeOH/H2O

Sources & evidence

ORD record
ord-cde277514664456ca8e7141b80cb7fa2
Source dataset
uspto-grants-1992_03
Patent number
US05098918

Reaction notes

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