Boron tribromide → HCID 136378061, compound

HRID 1920078Notes

Reaction equation

HRID 1920078 reaction equation
C[O:2][C:3]1[CH:4]=[C:5]([C:14]2[N:19]=[CH:18][N:17]=[C:16]([C:20]3[C:21]([C:27]([F:30])([F:29])[F:28])=[N+:22]([O-:26])[CH:23]=[CH:24][CH:25]=3)[N:15]=2)[CH:6]=[C:7]([N+:11]([O-:13])=[O:12])[C:8]=1[O:9]C.B(Br)(Br)Br>ClCCl>[OH:2][C:3]1[CH:4]=[C:5]([C:14]2[N:19]=[CH:18][N:17]=[C:16]([C:20]3[C:21]([C:27]([F:28])([F:30])[F:29])=[N+:22]([O-:26])[CH:23]=[CH:24][CH:25]=3)[N:15]=2)[CH:6]=[C:7]([N+:11]([O-:13])=[O:12])[C:8]=1[OH:9]

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 67036856HCID 67036856, compound

Product 1

HCID 136378061HCID 136378061, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-78 °C

Procedure

A portion of 3-(4-(3,4-dimethoxy-5-nitrophenyl)-1,3,5-triazin-2-yl)-2-(trifluoromethyl)pyridine 1-oxide (1.269 g, 3 mmol) was taken up in dichloromethane (25 mL). The yellowish solution was cooled to −78° C. under argon and boron tribromide (2.55 mL, 27 mmol) was added dropwise. The red reaction mixture was allowed to warm to room temperature and stirred for 18 hours and then carefully poured into ice-water (100 mL) and stirred for 1 hour. The yellow precipitate was filtered off, washed with water and dried over P2O5 under vacuum. Recrystallisation from a dichloromethane-ethanol mixture gave 3-(4-(3,4-dihydroxy-5-nitrophenyl)-1,3,5-triazin-2-yl)-2-(trifluoromethyl)pyridine 1-oxide as a yellow solid, 1.07 g (90%).

Workup

  1. customThe red reaction mixture
  2. temperatureto warm to room temperature
  3. stirringstirred for 1 hour
  4. filtrationThe yellow precipitate was filtered off
  5. washwashed with water
  6. dry with materialdried over P2O5 under vacuum
  7. customRecrystallisation from a dichloromethane-ethanol mixture

Sources & evidence

ORD record
ord-a1bba8fa05c34ff9b5f8daa2966ed9da
Source dataset
uspto-grants-2012_05
Patent number
US08168793B2

Reaction notes

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