Boron tribromide → HCID 136388718, compound

HRID 62003Notes

Reaction equation

HRID 62003 reaction equation
C[O:2][C:3]1[CH:4]=[C:5]([C:14]2[N:15]=[C:16]([C:20]3[C:21]([C:26]([F:29])([F:28])[F:27])=[N:22][CH:23]=[CH:24][CH:25]=3)[N:17]=[N:18][CH:19]=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:15]=[C:16]([C:20]3[C:21]([C:26]([F:29])([F:28])[F:27])=[N:22][CH:23]=[CH:24][CH:25]=3)[N:17]=[N:18][CH:19]=2)[CH:4]=[C:3]([OH:2])[C:8]=1[OH:9])([O-:13])=[O:12]

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 687018815-(3,4-Dimethoxy-5-nitrophenyl)-3-(2-(trifluoromethyl)pyridin-3-yl)-1,2,4-triazine

Product 1

HCID 136388718HCID 136388718, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-78 °C

Procedure

5-(3,4-dimethoxy-5-nitrophenyl)-3-(2-(trifluoromethyl)pyridin-3-yl)-1,2,4-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. The solid was recrystallised from dichloromethane-ethanol to give 3-nitro-5-(3-(2-(trifluoromethyl)pyridin-3-yl)-1,2,4-triazin-5-yl)benzene-1,2-diol as a yellow solid, 0.807 g (71%).

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. customThe solid was recrystallised from dichloromethane-ethanol

Sources & evidence

ORD record
ord-bb38d0def4ba47a591e0ebf2ddb0aa66
Source dataset
uspto-grants-2016_09
Patent number
US09446012B2

Reaction notes

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