Dimethylformamide → 7-Propyl-3-(trifluoromethyl)-6-(4-bromobutyloxy)-1,2-benzisoxazole

HRID 1245309Notes

Reaction equation

HRID 1245309 reaction equation
CN(C=O)C.[OH:6][C:7]1[CH:19]=[CH:18][C:10]2[C:11]([C:14]([F:17])([F:16])[F:15])=[N:12][O:13][C:9]=2[C:8]=1[CH2:20][CH2:21][CH3:22].[Br:23][CH2:24][CH2:25][CH2:26][CH2:27]Br.C(=O)([O-])[O-].[Cs+].[Cs+]>C(OCC)(=O)C.CCOCC>[CH2:20]([C:8]1[C:9]2[O:13][N:12]=[C:11]([C:14]([F:17])([F:16])[F:15])[C:10]=2[CH:18]=[CH:19][C:7]=1[O:6][CH2:27][CH2:26][CH2:25][CH2:24][Br:23])[CH2:21][CH3:22]

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 80561,4-DibromobutaneHCID 10796Cesium carbonateHCID 1358008127-Propyl-3-(trifluoromethyl)benzo[d]isoxazol-6-ol

Product 1

HCID 219109907-Propyl-3-(trifluoromethyl)-6-(4-bromobutyloxy)-1,2-benzisoxazole

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a DMF solution (50 mL) of 6-hydroxy-7-propyl-3-(trifluoromethyl)-1,2-benzisoxazole as prepared in Example 4 step 2 (6.5 gram, 26.5 mmol) was added 1,4-dibromobutane (16 mL, 133 mmol), followed by cesium carbonate (9.1 grams, 27.8 mmol). The mixture was stirred at room temperature overnight. After aqueous/ether work-up and silica gel chromatography (hexanes: 2.5% ethyl acetate), the title compound was obtained.

Sources & evidence

ORD record
ord-7cfd44608b1741178ad25b377a34f5fa
Source dataset
uspto-grants-2006_10
Patent number
US07125865B2

Reaction notes

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