Ammonium Chloride → HCID 90414084, compound

HRID 1746051Notes

Reaction equation

Br[C:2]1[CH:3]=[CH:4][C:5]2[O:9][CH2:8][S:7][C:6]=2[CH:10]=1.[Li]CCCC.[CH3:16][C:17]1([CH3:24])[C:21]([CH3:23])([CH3:22])[O:20][BH:19][O:18]1.[NH4+].[Cl-]>O1CCCC1>[O:9]1[C:5]2[CH:4]=[CH:3][C:2]([B:19]3[O:20][C:21]([CH3:23])([CH3:22])[C:17]([CH3:24])([CH3:16])[O:18]3)=[CH:10][C:6]=2[S:7][CH2:8]1

Participants

Conditions

Temperature: -70 °C

Procedure

5-Bromobenzo[d][1,3]oxathiole (1.0 g, 4.6 mmol, prepared as described in Cabiddu, Salvatore; Cerioni, Giovanni; Cocco, Maria Teresa; Maccioni, Antonio; Plumitallo, Antonio, Journal of Heterocyclic Chemistry 1982, 19, 135-139) was dissolved in dry tetrahydrofuran (12 mL), cooled to −70° C., treated in portions with n-BuLi (2.5 M; 1.9 mL, 4.8 mmol) and stirred at −70° C. for 30 min. 4,4,5,5-Tetramethyl-1,3,2-dioxaborolane (900 mg, 4.8 mmol) was added and stirring was continued for 1.5 h during which the temperature rose to −30° C. The mixture was treated with saturated NH4Cl (5 mL) and extracted with ethyl acetate (2×25 mL). The combined extracts were washed with saturated NaCl (10 mL), dried (Na2SO4) and evaporated to give the title compound which was used without further purification (1.2 g, 99%): 1H NMR (400 MHz, CDCl3) δ 7.62 (d, J=1.1 Hz, 1H), 7.48 (dd, J=8.0, 1.3 Hz, 1H), 6.82 (d, J=8.1 Hz, 1H), 5.69 (s, 2H), 1.32 (s, 12H); EIMS m/z 264.

Workup

stirringstirring
waitwas continued for 1.5 h during which
customrose to −30° C
extractionextracted with ethyl acetate (2×25 mL)
washThe combined extracts were washed with saturated NaCl (10 mL)
dry with materialdried (Na2SO4)
customevaporated

Sources & evidence

ORD record: ord-05f91508ad484bac909b14f77b2fdb07
Source dataset: uspto-grants-2015_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09149038B2

Reaction notes

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