Boron tribromide → HCID 67852482, compound

HRID 1464008Notes

Reaction equation

HRID 1464008 reaction equation
C[O:2][C:3]1[C:4]([Cl:22])=[CH:5][C:6]2[CH2:12][CH2:11][N:10]([CH3:13])[C@@H:9]3[CH2:14][C:15]4[C:20]([C@H:8]3[C:7]=2[CH:21]=1)=[CH:19][CH:18]=[CH:17][CH:16]=4.B(Br)(Br)[Br:24]>C(Cl)Cl>[BrH:24].[OH:2][C:3]1[C:4]([Cl:22])=[CH:5][C:6]2[CH2:12][CH2:11][N:10]([CH3:13])[C@@H:9]3[CH2:14][C:15]4[C:20]([C@H:8]3[C:7]=2[CH:21]=1)=[CH:19][CH:18]=[CH:17][CH:16]=4

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 14371634HCID 14371634, compound

Product 1

HCID 67852482HCID 67852482, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 147 mg (0.47 mmol) of Compound Q from Step F above in 10 mL methylene chloride at -78° C. was treated with 90 mL boron tribromide, and the mixture was stirred for 4 hours while coming to room temperature. The reaction was quenched with 10 mL dry methanol and stirred for 10 minutes. The solvent was evaporated under reduced pressure, and the residue was treated with a second 10 mL portion of methanol. After 10 minutes, the solvent was evaporated at 10 mm Hg and 50° C. for 45 minutes to give 180 mg (100%) of the crude hydrobromide, 200 MHz NMR(d6-DMSO) d 2.97(s,3H), 2.90-3.90(m,7H),5.02(d,1H,J=8 Hz),6.99(s,1H),7.36(m,5H).

Workup

  1. customwhile coming to room temperature
  2. customThe reaction was quenched with 10 mL dry methanol
  3. stirringstirred for 10 minutes
  4. customThe solvent was evaporated under reduced pressure
  5. additionthe residue was treated with a second 10 mL portion of methanol
  6. waitAfter 10 minutes
  7. customthe solvent was evaporated at 10 mm Hg and 50° C. for 45 minutes

Sources & evidence

ORD record
ord-6068bb81463d49b289e4d6b37846b40c
Source dataset
uspto-grants-1994_04
Patent number
US05302716

Reaction notes

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