5-Nitro-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzenemethanol → 5-nitrobenzo[c][1,2]oxaborol-1(3H)-ol

HRID 1425931Notes

Reaction equation

HRID 1425931 reaction equation
[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([B:12]2[O:16][C:15](C)(C)C(C)(C)[O:13]2)=[C:8](CO)[CH:9]=1)([O-:3])=[O:2]>Cl>[N+:1]([C:4]1[CH:9]=[CH:8][C:7]2[B:12]([OH:13])[O:16][CH2:15][C:6]=2[CH:5]=1)([O-:3])=[O:2]

Participants

3

Reactant 1

HCID 682814405-Nitro-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzenemethanol

Product 1

HCID 682814365-nitrobenzo[c][1,2]oxaborol-1(3H)-olYield 99.8%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

(5-Nitro-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)methanol (CI) (1.25 g, 4.48 mmol) was dissolved in 6 M HCl (100 mL) at 60° C. and stirred overnight. The mixture was then cooled to the room temperature and extracted with EtOAc (2×100 mL). The organic layers were combined, washed with brine and dried over anhydrous MgSO4 to give 5-nitrobenzo[c][1,2]oxaborol-1(3H)-ol (CII) as a brown solid (800 mg, 4.47 mmol, 99% yield). The crude product was used without further purification for step 4. ESIMS found for C7H6BNO4 m/z 180.1 (M+H).

Workup

  1. extractionextracted with EtOAc (2×100 mL)
  2. washwashed with brine
  3. dry with materialdried over anhydrous MgSO4

Sources & evidence

ORD record
ord-be9537d66efd4407a1afde4643670a82
Source dataset
uspto-grants-2015_01
Patent number
US08933018B2

Reaction notes

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