Boron tribromide → HCID 136378046, compound

HRID 62005Notes

Reaction equation

HRID 62005 reaction equation
C[O:2][C:3]1[CH:4]=[C:5]([C:14]2[N:19]=[C:18]([C:20]3[C:21]([C:26]([F:29])([F:28])[F:27])=[N:22][CH:23]=[CH:24][CH:25]=3)[N:17]=[CH:16][N:15]=2)[CH:6]=[C:7]([N+:11]([O-:13])=[O:12])[C:8]=1[O:9]C.B(Br)(Br)Br>ClCCl>[N+:11]([C:7]1[CH:6]=[C:5]([C:14]2[N:19]=[C:18]([C:20]3[C:21]([C:26]([F:29])([F:28])[F:27])=[N:22][CH:23]=[CH:24][CH:25]=3)[N:17]=[CH:16][N:15]=2)[CH:4]=[C:3]([OH:2])[C:8]=1[OH:9])([O-:13])=[O:12]

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 687052912-(3,4-Dimethoxy-5-nitrophenyl)-4-(2-(trifluoromethyl)pyridin-3-yl)-1,3,5-triazine

Product 1

HCID 136378046HCID 136378046, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-78 °C

Procedure

A portion of 2-(3,4-dimethoxy-5-nitrophenyl)-4-(2-(trifluoromethyl)pyridin-3-yl)-1,3,5-triazine (1.221 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. It was 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-nitro-5-(4-(2-(trifluoro-methyl)pyridin-3-yl)-1,3,5-triazin-2-yl)benzene-1,2-diol as a yellow solid, 0.966 g (85%).

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-91ff1e7e60ce44668ea8924c3e745a51
Source dataset
uspto-grants-2016_09
Patent number
US09446012B2

Reaction notes

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