Boron tribromide → HCID 68702434, compound

HRID 42656Notes

Reaction equation

HRID 42656 reaction equation
C[O:2][C:3]1[CH:4]=[C:5]([C:14]2[N:15]=[C:16]([C:19]3[C:20]([C:25]([F:28])([F:27])[F:26])=[N:21][CH:22]=[CH:23][CH:24]=3)[O:17][CH:18]=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:19]3[C:20]([C:25]([F:28])([F:27])[F:26])=[N:21][CH:22]=[CH:23][CH:24]=3)[O:17][CH:18]=2)[CH:4]=[C:3]([OH:2])[C:8]=1[OH:9])([O-:13])=[O:12]

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 687013284-(3,4-Dimethoxy-5-nitrophenyl)-2-(2-(trifluoromethyl)pyridin-3-yl)oxazole

Product 1

HCID 68702434HCID 68702434, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-78 °C

Procedure

4-(3,4-dimethoxy-5-nitrophenyl)-2-(2-(trifluoromethyl)pyridin-3-yl)oxazole (1.185 g, 3 mmol) was taken up in dichloromethane (25 mL). The yellowish suspension 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 resulting yellow precipitate was filtered off, washed with water and dried over P2O5 under vacuum. The solid was recrystallized from ethanol to give 3-nitro-5-(2-(2-(trifluoromethyl)pyridin-3-yl)oxazol-4-yl)benzene-1,2-diol as a yellow solid, 0.627 g, (57%).

Workup

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

Sources & evidence

ORD record
ord-52bbb6c1708a4173a55abebf73778dc1
Source dataset
uspto-grants-2013_09
Patent number
US08536203B2

Reaction notes

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