Nitric Acid → HCID 68281454, compound

HRID 1425942Notes

Reaction equation

HRID 1425942 reaction equation
[F:1][C:2]([F:14])([F:13])[C:3]1[C:11]2[CH2:10][O:9][B:8]([OH:12])[C:7]=2[CH:6]=[CH:5][CH:4]=1.[N+:15]([O-])([OH:17])=[O:16]>>[N+:15]([C:5]1[CH:4]=[C:3]([C:2]([F:1])([F:13])[F:14])[C:11]2[CH2:10][O:9][B:8]([OH:12])[C:7]=2[CH:6]=1)([O-:17])=[O:16]

Participants

3

Reactant 2

HCID 944Nitric AcidHCID 682815094-(trifluoromethyl)benzo[c][1,2]oxaborol-1(3H)-ol

Product 1

HCID 68281454HCID 68281454, compoundYield 66%

Conditions

Temperature
-40 °C

Procedure

To 4-(trifluoromethyl)benzo[c][1,2]oxaborol-1(3H)-ol (CXXX) (1.17 g, 5.79 mmol) cooled to −40° C. was slowly added HNO3 (10 mL, 99%). The reaction mixture was stirred for 3 h at −40° C. and then slowly quenched with crushed ice. The yellow precipitate was filtered and washed with hexane to produce 6-nitro-4-(trifluoromethyl)benzo[c][1,2]oxaborol-1(3H)-ol (CXXXI) as a yellow crystalline solid (950 mg, 3.83 mmol, 66% yield). ESIMS found for C8H5BF3NO4 m/z 246.4 (M−H).

Workup

  1. customslowly quenched with crushed ice
  2. filtrationThe yellow precipitate was filtered
  3. washwashed with hexane

Sources & evidence

ORD record
ord-733ea9213b55418d98fcab3facbf94f1
Source dataset
uspto-grants-2015_01
Patent number
US08933018B2

Reaction notes

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