Boron tribromide → HCID 18433429, compound

HRID 2305964Notes

Reaction equation

HRID 2305964 reaction equation
[CH:1]1([N:5]([CH3:28])[C:6](=[O:27])[C:7]2[CH:12]=[C:11]([O:13][C:14]3[C:19]([CH3:20])=[CH:18][C:17]([N+:21]([O-:23])=[O:22])=[CH:16][C:15]=3[CH3:24])[CH:10]=[CH:9][C:8]=2[O:25]C)[CH2:4][CH2:3][CH2:2]1.B(Br)(Br)Br>O>[CH:1]1([N:5]([CH3:28])[C:6](=[O:27])[C:7]2[CH:12]=[C:11]([O:13][C:14]3[C:19]([CH3:20])=[CH:18][C:17]([N+:21]([O-:23])=[O:22])=[CH:16][C:15]=3[CH3:24])[CH:10]=[CH:9][C:8]=2[OH:25])[CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 22728151HCID 22728151, compound

Product 1

HCID 18433429HCID 18433429, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

N-Cyclobutyl-5-(2,6-dimethyl-4-nitro-phenoxy)-2-hydroxy-N-methyl-benzamide was prepared from N-cyclobutyl-5-(2,6-dimethyl-4-nitro-phenoxy)-2-methoxy-N-methyl-benzamide according to a procedure analogous to that described in EXAMPLE 2, Step B. Boron tribromide (1M in dichloromethane, 2.0 equiv) was used. After water addition, the mixture was extracted with dichloromethane (3×10 ml). The combined organic phases were dried over anhydrous Na2SO4, filtered, and concentrated. The title product of Step E was used in the next step without purification. MS (APCI+) Calc.: 370.4, Found: 371.1 (M+1).

Workup

  1. extractionthe mixture was extracted with dichloromethane (3×10 ml)
  2. dry with materialThe combined organic phases were dried over anhydrous Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe title product of Step E was used in the next step without purification

Sources & evidence

ORD record
ord-c06604e91acc40abb1c32d870a120a5b
Source dataset
uspto-grants-2002_08
Patent number
US06441015B2

Reaction notes

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