Boron tribromide → HCID 20765600, compound

HRID 1815520Notes

Reaction equation

HRID 1815520 reaction equation
B(Br)(Br)Br.[Cl:5][C:6]1[C:16]([Cl:17])=[C:15]([S:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=2[O:25]C)[CH:14]=[CH:13][C:7]=1[CH:8]=[CH:9][C:10]([OH:12])=[O:11]>C(Cl)Cl>[OH:25][C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=1[S:18][C:15]1[CH:14]=[CH:13][C:7](/[CH:8]=[CH:9]/[C:10]([OH:12])=[O:11])=[C:6]([Cl:5])[C:16]=1[Cl:17]

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 68984012HCID 68984012, compound

Product 1

HCID 20765600HCID 20765600, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Boron tribromide (84 mL of a 1.0M solution in CH2Cl2) was added to a suspension of Example 310C in CH2Cl2 (85 mL) at 0° C. After addition was completed, the ice-water bath was removed, and the homogeneous dark solution was stirred for 2 hours before the mixture was poured into 1 N aqueous HCl (100 mL) and ice (100 g), and extracted with EtOAc (3×100 mL). ). The organic layers were combined, washed with brine (1×50 mL), dried (MgSO4), filtered, and concentrated to a white solid (11.3 g). 1H NMR (DMSO-d6, 300 MHz) δ 10.26 (s, 1H), 7.82 (d, J15.6, 1H), 7.74 (d, J=8.5 Hz, 1H), 7.44 (dt, J=7.8 Hz, J=1.7 Hz, 1H), 7.41 (dd, J=7.4 Hz, J=1.7 Hz, 1H), 7.05 (dd, J=8.4 Hz, J=1.3 Hz, 1H), 6.94 (dt, J=7.8 Hz, J=1.4 Hz, 1H), 6.52 (d, J=8.2 Hz, 1H), 6.50 (d, J=16.0 Hz, 1H); MS (APCI) m/z 339 (M−H)−, 375 (M+Cl)−.

Workup

  1. additionAfter addition
  2. customthe ice-water bath was removed
  3. additionwas poured into 1 N aqueous HCl (100 mL) and ice (100 g)
  4. extractionextracted with EtOAc (3×100 mL)
  5. washwashed with brine (1×50 mL)
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated to a white solid (11.3 g)

Sources & evidence

ORD record
ord-d0daf340c3f54077bf9688a5250103d3
Source dataset
uspto-grants-2005_04
Patent number
US06878700B1

Reaction notes

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