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

HRID 1172829Notes

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

Participants

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

extractionThe aqueous layer was extracted with ethyl acetate
washThe combine organic phase was washed with brine
dry with materialdried over magnesium sulfate
concentrationconcentrated
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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