Boron tribromide → HCID 18433431, compound

HRID 2305959Notes

Reaction equation

HRID 2305959 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([Cl:27])[C:9]=1[O:10][C:11]1[CH:16]=[CH:15][C:14]([O:17]C)=[C:13]([C:19]([N:21]2[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]2)=[O:20])[CH:12]=1)[C:5]#[N:6].B(Br)(Br)Br.C(=O)(O)[O-].[Na+]>O>[Cl:27][C:8]1[CH:7]=[C:4]([CH:3]=[C:2]([Cl:1])[C:9]=1[O:10][C:11]1[CH:16]=[CH:15][C:14]([OH:17])=[C:13]([C:19]([N:21]2[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]2)=[O:20])[CH:12]=1)[C:5]#[N:6]

Participants

5

Reactant 3

HCID 25134Boron tribromideHCID 516892Sodium BicarbonateHCID 18433435HCID 18433435, compound

Product 1

HCID 18433431HCID 18433431, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

3,5-Dichloro-4-[4-hydroxy-3-(piperidine-1-carbonyl)-phenoxy]-benzonitrile was prepared from 3,5-dichloro-4-[4-methoxy-3-(piperidine-1-carbonyl)-phenoxy]-benzonitrile 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 stirred for 30 minutes at RT, then basified with aqueous saturated sodium bicarbonate solution, and 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.: 390.0, Found: 391.1 (M+1).

Workup

  1. extractionextracted 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-8cf00e58410a4440b6523168f8ace387
Source dataset
uspto-grants-2002_08
Patent number
US06441015B2

Reaction notes

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