Boron tribromide → HCID 18439755, compound

HRID 457570Notes

Reaction equation

HRID 457570 reaction equation
B(Br)(Br)Br.[Br:5][C:6]1[O:7][C:8]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([O:17]C)[CH:12]=2)=[CH:9][N:10]=1>ClCCl>[Br:5][C:6]1[O:7][C:8]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([OH:17])[CH:12]=2)=[CH:9][N:10]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 18439758HCID 18439758, compound

Product 1

HCID 18439755HCID 18439755, compoundYield 47.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Boron tribromide (5.0 mL, 13.25 g, 53 mmol) was added dropwise to a stirred solution of 2-bromo-5-(3-methoxyphenyl)-1,3-oxazole (2.1 g, 10 mmol) in dry dichloromethane (50 mL) at RT under Nitrogen. The reaction mixture was stirred for about 1 h and then carefully poured over ice. After the ice melted, the mixture was extracted with ethyl acetate (2×250 mL). The combined organic extracts were dried over anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure. The resulting solid was collected by filtration and dried under vacuum to afford a light brown solid (1.13 g, 47%). 1H NMR (400 MHz, d6-DMSO): δ 6.74 (dd, J1=8.1, J2=2.2, 1H), 6.99 (d, J=2, 1H), 7.05 (d, J=7.9, 1H), 7.21 (t, J=7.9, 1H), 7.64 (s, 1H), 9.48 (bs, 1H).

Workup

  1. additioncarefully poured over ice
  2. extractionthe mixture was extracted with ethyl acetate (2×250 mL)
  3. dry with materialThe combined organic extracts were dried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. filtrationThe resulting solid was collected by filtration
  7. customdried under vacuum

Sources & evidence

ORD record
ord-65f2ce8ca6b84622ae7ed48ca64e2211
Source dataset
uspto-grants-2007_03
Patent number
US07189712B2

Reaction notes

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