Water → HCID 9901789, compound

HRID 2305957Notes

Reaction equation

HRID 2305957 reaction equation
[CH:1]([C:4]1[CH:5]=[C:6]([CH:21]=[CH:22][C:23]=1[O:24]C)[O:7][C:8]1[C:13]([CH3:14])=[CH:12][C:11]([C:15]2[N:16]=[N:17][NH:18][N:19]=2)=[CH:10][C:9]=1[CH3:20])([CH3:3])[CH3:2].B(Br)(Br)Br.O>C(Cl)(Cl)Cl>[CH3:14][C:13]1[CH:12]=[C:11]([C:15]2[N:16]=[N:17][NH:18][N:19]=2)[CH:10]=[C:9]([CH3:20])[C:8]=1[O:7][C:6]1[CH:21]=[CH:22][C:23]([OH:24])=[C:4]([CH:1]([CH3:3])[CH3:2])[CH:5]=1

Participants

5

Reactant 3

HCID 962WaterHCID 25134Boron tribromide2×HCID 18433439HCID 18433439, compound

Product 1

HCID 9901789HCID 9901789, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of 5-[4-(3-isopropyl-4-methoxy-phenoxy)-3,5-dimethyl-phenyl]-2H-tetrazole (26 mg, 0.077 mmol) in 6 ml of chloroform at RT was added boron tribromide (1M in dichloromethane, 0.12 ml, 0.12 mmol). The reaction was stirred for 20 hours at RT, then additional boron tribromide (1M in dichloromethane, 0.3 ml) was added, and the reaction was stirred at RT for 6 hours. Water (10 ml) was added, and the reaction was stirred for 1 hour at RT, then extracted with ethyl acetate (3×15 ml), dried, and concentrated. The white solid residue was triturated with dichloromethane (2×0.3 ml) and dried in vacuo to afford the title product of Example 1. MS (APCI−) Calc.: 324.4, Found: 323.3 (M−1).

Workup

  1. stirringthe reaction was stirred at RT for 6 hours
  2. stirringthe reaction was stirred for 1 hour at RT
  3. extractionextracted with ethyl acetate (3×15 ml)
  4. customdried
  5. concentrationconcentrated
  6. customThe white solid residue was triturated with dichloromethane (2×0.3 ml)
  7. customdried in vacuo

Sources & evidence

ORD record
ord-869b31ea9993434d9444af6bce17db60
Source dataset
uspto-grants-2002_08
Patent number
US06441015B2

Reaction notes

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