Triisopropyl borate → HCID 178425957, compound

HRID 252269Notes

Reaction equation

Br[C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][C:12]([CH3:15])([CH3:14])[CH3:13])(=[O:10])=[O:9])=[CH:4][C:3]=1[CH3:16].[B:17](OC(C)C)([O:22]C(C)C)[O:18]C(C)C.C([Li])CCC>O1CCCC1>[BH:17]([OH:22])[OH:18].[C:12]([NH:11][S:8]([C:5]1[CH:6]=[CH:7][CH:2]=[C:3]([CH3:16])[CH:4]=1)(=[O:9])=[O:10])([CH3:15])([CH3:14])[CH3:13]

Participants

Conditions

Temperature: -78 °C

Procedure

4-Bromo-N-tert-butyl-3-methyl-benzenesulfonamide (10 g, 32.6 mmol) was dissolved in dry tetrahydrofurane, then cooled to −78° C. Triisopropyl borate (27.7 ml, 120.8 mmol, 3.7 equiv.) was added in one portion, followed by the dropwise addition of n-butyllithium solution 1.6M (75.5 ml, 120.8 mmol, 3.7 equiv.) at −78° C. The mixture was stirred overnight, then quenched dropwise with water. The organic solvent was evaporated and the pH adjusted to 3 with 0.5 M HCl. The residue was extracted with ethyl acetate and the combined organic extracts were washed with brine, dried over magnesiumsulfat-dihydrate, filtered and evaporated. The crude product was purified on silica-gel with ethyl acetate/n-heptane to give 2.82 g of the title product as yellow, waxy solid. MS (ES): m/e 270 (M−H)

Workup

customquenched dropwise with water
customThe organic solvent was evaporated
extractionThe residue was extracted with ethyl acetate
washthe combined organic extracts were washed with brine
dry with materialdried over magnesiumsulfat-dihydrate
filtrationfiltered
customevaporated
customThe crude product was purified on silica-gel with ethyl acetate/n-heptane

Sources & evidence

ORD record: ord-c0532b2af963488f8d54c815be1558c7
Source dataset: uspto-grants-2011_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07868030B2

Reaction notes

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