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Heptane → 6-Chloro-3-[4-(4-chlorophenoxy)-2-propylphenyl]-1,2-benzisoxazol-5-ol

HRID 1172829
Notes
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Reaction equation

HRID 1172829 reaction equation
[Cl:1][C:2]1[C:27]([O:28]C)=[CH:26][C:5]2[C:6]([C:9]3[CH:14]=[CH:13][C:12]([O:15][C:16]4[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][CH:17]=4)=[CH:11][C:10]=3[CH2:23][CH2:24][CH3:25])=[N:7][O:8][C:4]=2[CH:3]=1.B(Br)(Br)Br.CCCCCCC.C(=O)(O)[O-].[Na+]>ClCCl>[Cl:1][C:2]1[C:27]([OH:28])=[CH:26][C:5]2[C:6]([C:9]3[CH:14]=[CH:13][C:12]([O:15][C:16]4[CH:17]=[CH:18][C:19]([Cl:22])=[CH:20][CH:21]=4)=[CH:11][C:10]=3[CH2:23][CH2:24][CH3:25])=[N:7][O:8][C:4]=2[CH:3]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 8900HeptaneHCID 25134Boron tribromideHCID 516892Sodium BicarbonateHCID 686921166-Chloro-3-[4-(4-chlorophenoxy)-2-propylphenyl]-5-methoxy-1,2-benzisoxazole

Product 1

HCID 686911006-Chloro-3-[4-(4-chlorophenoxy)-2-propylphenyl]-1,2-benzisoxazol-5-ol

Reagents, catalysts & solvents 1

HCID 6344
Dichloromethane
Solvent

Conditions

Temperature
25 °C

Procedure

To a solution of the product from Step 5 (0.82 g, 1.9 mmol) in dichloromethane (15 mL) cooled at 0° C. was added a solution of boron tribromide in heptane (1.0 M, 3.8 mL, 3.8 mmol). The reaction was stirred at 25° C. for 30 min and then poured into aqueous sodium bicarbonate. The aqueous layer was extracted with ethyl acetate. The combine organic phase was washed with brine, dried over magnesium sulfate and concentrated. The residue was purified by chromatography on silica gel to give the title product.

Workup

  1. extractionThe aqueous layer was extracted with ethyl acetate
  2. washThe combine organic phase was washed with brine
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated
  5. customThe residue was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-5bb5df3d398c441bb3fd8c1a25264100
Source dataset
uspto-grants-2010_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07834036B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes