Boron tribromide → HCID 178428375, compound

HRID 2305962Notes

Reaction equation

HRID 2305962 reaction equation
[CH:1]([C:4]1[CH:5]=[C:6]([CH:22]=[CH:23][C:24]=1[O:25]C)[O:7][C:8]1[C:13]([CH3:14])=[CH:12][C:11]([NH:15][C:16]2[NH:20][N:19]=[N:18][N:17]=2)=[CH:10][C:9]=1[CH3:21])([CH3:3])[CH3:2].B(Br)(Br)Br>O>[CH3:14][C:13]1[CH:12]=[C:11]([NH:15][C:16]2[NH:20][N:19]=[N:18][N:17]=2)[CH:10]=[C:9]([CH3:21])[C:8]=1[O:7][C:6]1[CH:22]=[CH:23][C:24]([OH:25])=[C:4]([CH:1]([CH3:3])[CH3:2])[CH:5]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 178492471HCID 178492471, compound

Product 1

HCID 178428375HCID 178428375, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

4-[2,6-Dimethyl-4-(1H-tetrazol-5-ylamino)-phenoxy]-2-isopropyl-phenol was prepared from [4-(3-isopropyl-4-methoxy-phenoxy)-3,5-dimethyl-phenyl]-(1H-tetrazol-5-yl)-amine according to a procedure analogous to that described in EXAMPLE 2, Step B. Boron tribromide (1M in dichloromethane, 8.0 equiv) was used. After water addition, the mixture was extracted with ethyl acetate (3×10 ml). The combined organic phases were dried over anhydrous Na2SO4, filtered, and concentrated. The residue was purified by preparative TLC (methanol:water:dichloromethane 25:3:72) to afford the title product of Example 4. MS (APCI+) Calc.: 339.4, Found: 340.1 (M+1).

Workup

  1. extractionthe mixture was extracted with ethyl acetate (3×10 ml)
  2. dry with materialThe combined organic phases were dried over anhydrous Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue was purified by preparative TLC (methanol:water:dichloromethane 25:3:72)

Sources & evidence

ORD record
ord-8dcff98b1c4e42c69338a0b394319756
Source dataset
uspto-grants-2002_08
Patent number
US06441015B2

Reaction notes

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