Triethylamine → Phosphoric acid 3-[3-(4-bromo-phenyl)-benzo [d]isothiazol-6-yl]-1,1-dimethyl-prop-2-ynyl ester diethyl ester

HRID 966354Notes

Reaction equation

[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:12]3[CH:13]=[CH:14][C:15]([C:17]#[C:18][C:19]([CH3:22])([OH:21])[CH3:20])=[CH:16][C:11]=3[S:10][N:9]=2)=[CH:4][CH:3]=1.[Li+].CCC[CH2-].C(N(CC)CC)C.[CH2:35]([O:37][P:38](Cl)([O:40][CH2:41][CH3:42])=[O:39])[CH3:36]>C1COCC1.CCCCCC.O>[CH2:35]([O:37][P:38](=[O:39])([O:40][CH2:41][CH3:42])[O:21][C:19]([CH3:22])([CH3:20])[C:18]#[C:17][C:15]1[CH:14]=[CH:13][C:12]2[C:8]([C:5]3[CH:4]=[CH:3][C:2]([Br:1])=[CH:7][CH:6]=3)=[N:9][S:10][C:11]=2[CH:16]=1)[CH3:36]

Participants

Conditions

Temperature: 0 °C

Procedure

200 mg (0.54 mmol) 4-[3-(4-Bromo-phenyl)-benzo[d]isothiazol-6-yl]-2-methyl-but-3-yn-2-ol in 2 ml THF were treated with 36 μl (5.6 mmol) 1.6 M N-Butyllithium in hexane at −78° C. for 30 min. 112 μl (0.81 mmol, 1.5 eq) Triethylamine in 0.5 ml THF and 117 μl (0.8 mmol, 1.5 eq) Diethylchlorophosphate in 0.5 ml THF were added and the solution was stirred at −78° C. over night and at 0° C. for 4 h. Water was added, and the inorganic phase was extracted with EtOAc, the combined organic phases were washed with brine and dried over Na2SO4. Column chromatography on silica gel with hexane:EtOAc 3:1 gave 90 mg (33%) Phosphoric acid 3-[3-(4-bromo-phenyl)-benzo[d]isothiazol-6-yl]-1,1-dimethyl-prop-2-ynyl ester diethyl ester as yellow semisolid, MS: 508 (MH+, 1Br).

Workup

extractionthe inorganic phase was extracted with EtOAc
washthe combined organic phases were washed with brine
dry with materialdried over Na2SO4

Sources & evidence

ORD record: ord-9f5ff56b48884f87b3d6af591d23d7e2
Source dataset: uspto-grants-2005_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06951879B2

Reaction notes

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