Benzyl Bromide → HCID 178478223, compound

HRID 1828076Notes

Reaction equation

HRID 1828076 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[C:4]([C:9]2[CH:13]=[CH:12][NH:11][N:10]=2)[CH:3]=1.C([O-])([O-])=O.[K+].[K+].[CH2:20](Br)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>CC(C)=O>[CH2:20]([O:8][C:5]1[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][C:4]=1[C:9]1[CH:13]=[CH:12][NH:11][N:10]=1)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 1785160624-Chloro-2-(1H-pyrazol-3-yl)phenol

Product 1

HCID 178478223HCID 178478223, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a stirred solution of 4-chloro-2-(1H-pyrazol-3-yl)-phenol (1 g, CAS 18704-67-1) at r.t. in acetone (20 ml) under an argon atmosphere were added K2CO3 (746 mg) and benzylbromid (0.61 ml). The reaction mixture was stirred at r.t. for 21 h. The solids were filtered off and washed with acetone. The filtrate was concentrated to leave a light orange oil. The crude product was purified by chromatography (silica gel, cyclohexane/ethyl acetate 2:1) to give 3-(2-benzyloxy-5-chloro-phenyl)-1H-pyrazole as off-white solid. MS 284.8 ([M+H]+)

Workup

  1. filtrationThe solids were filtered off
  2. washwashed with acetone
  3. concentrationThe filtrate was concentrated
  4. customto leave a light orange oil
  5. customThe crude product was purified by chromatography (silica gel, cyclohexane/ethyl acetate 2:1)

Sources & evidence

ORD record
ord-74ee45f55a204c1eb34118994f0c0df5
Source dataset
uspto-grants-2006_06
Patent number
US07056932B2

Reaction notes

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