Hydrochloric Acid → HCID 57968891, compound

HRID 1483772Notes

Reaction equation

[N+:1]([C:4]1[CH:26]=[CH:25][C:7]([O:8][C:9]2[CH:10]=[CH:11][C:12]([B:17]3[O:21]C(C)(C)C(C)[O:18]3)=[C:13]([CH:16]=2)[CH:14]=O)=[CH:6][CH:5]=1)([O-:3])=[O:2].[BH4-].[Na+].Cl.C([O-])(O)=O.[Na+]>CCO.O>[N+:1]([C:4]1[CH:26]=[CH:25][C:7]([O:8][C:9]2[CH:10]=[CH:11][C:12]3[B:17]([OH:18])[O:21][CH2:14][C:13]=3[CH:16]=2)=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

Conditions

Temperature: 0 °C

Procedure

To a suspension of 5-(4-nitro-phenoxy)-2-(4,4,5-trimethyl-[1,3,2]dioxaborolan-2-yl)-benzaldehyde (721 mg, 1.9 mmol, 1.0 eq.) in EtOH (15 mL) at 0° C. was added NaBH4 (73.8 mg, 1.9 mmol, 1.0 eq.) in small portions. The mixture was stirred at 0° C. for 20 minutes and allowed to warm to room temperature in another 1 h. After cooling to 0° C., the clear solution was carefully treated with H2O (1 mL), followed by slow addition of HCl (5 mL, 3N). The resulting yellow suspension was allowed to ward to room temperature gradually and stirred for 2 h. The mixture was then treated with sat. NaHCO3 drop wise until PH reaching 7. The precipitate was collected by filtration, washed with H2O to give 5-(4-nitro-phenoxy)-3H-benzo[c][1,2]oxaborol-1-ol as a white powder. LCMS (m/z) 294 (M+23); 1H NMR (DMSO-d6) δ: 7.26 (d, J=8.6 Hz, 1H), 6.93 (d, J=3.0 Hz, 1H), 6.56 (dd, J=8.5, 3.0 Hz, 1H), 4.37 (s, 2H). Amount obtained, 510 mg, 96.4% yield.

Workup

temperatureto warm to room temperature in another 1 h
temperatureAfter cooling to 0° C.
customto ward to room temperature
stirringstirred for 2 h
filtrationThe precipitate was collected by filtration
washwashed with H2O

Sources & evidence

ORD record: ord-e8958849431f4368a8da514525b4b82c
Source dataset: uspto-grants-2016_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09416146B2

Reaction notes

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