Boron tribromide → HCID 11776983, compound

HRID 457567Notes

Reaction equation

HRID 457567 reaction equation
C[O:2][C:3]1[CH:4]=[C:5]([C:9]2[O:13][C:12]([NH:14][C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)=[N:11][CH:10]=2)[CH:6]=[CH:7][CH:8]=1.B(Br)(Br)Br>ClCCl>[NH:14]([C:12]1[O:13][C:9]([C:5]2[CH:4]=[C:3]([OH:2])[CH:8]=[CH:7][CH:6]=2)=[CH:10][N:11]=1)[C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 10038541HCID 10038541, compound

Product 1

HCID 11776983HCID 11776983, compoundYield 1,092.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of the title compound of Example 1 (0.110 g, 0.41 mmol) in dichloromethane (5 mL) was carefully treated with boron tribromide (0.516 g, 2.06 mmol). After stirring for 1 h, the reaction was carefully poured over ice. After the ice melted, the mixture was extracted with ethyl acetate (2×250 mL). The combined organic layers were dried over anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure. The title compound was dried under vacuum at RT 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. additionthe reaction was carefully poured over ice
  2. extractionthe mixture was extracted with ethyl acetate (2×250 mL)
  3. dry with materialThe combined organic layers were dried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. dry with materialThe title compound was dried under vacuum at RT

Sources & evidence

ORD record
ord-ad28cc81ffeb48858a570c61b770331b
Source dataset
uspto-grants-2007_03
Patent number
US07189712B2

Reaction notes

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