Boron tribromide → HCID 21476503, compound

HRID 2293154Notes

Reaction equation

HRID 2293154 reaction equation
Cl.C[O:3][C:4]1[CH:5]=[CH:6][CH:7]=[C:8]2[C:13]=1[N:12]=[C:11]([NH:14][C:15]1[CH:20]=[CH:19][C:18]([F:21])=[CH:17][C:16]=1[CH3:22])[N:10]=[C:9]2[N:23]1[CH2:32][CH2:31][C:30]2[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=2)[CH:24]1[CH3:33].BrB(Br)Br>ClCCl>[OH:3][C:4]1[CH:5]=[CH:6][CH:7]=[C:8]2[C:13]=1[N:12]=[C:11]([NH:14][C:15]1[CH:20]=[CH:19][C:18]([F:21])=[CH:17][C:16]=1[CH3:22])[N:10]=[C:9]2[N:23]1[CH2:32][CH2:31][C:30]2[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=2)[CH:24]1[CH3:33]

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 21476498HCID 21476498, compound

Product 1

HCID 21476503HCID 21476503, compoundYield 65.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of 4.1 g of the compound(9.6 mM) prepared in Example 34 and 50 ml of dichloromethane, 48 ml of tribromoboran was added at 0° C. The resultant was stirred at room temperature for 14 hours and then poured into ice water. The solids produced were filtered, dissolved in dichloromethane, and neutralized by adding aqueous NaOH solution. The dichloromethane layer was separated, dried over anhydrous sodium sulfate and concentrated to give 2.4 g of the title compound.

Workup

  1. additionwas added at 0° C
  2. customThe solids produced
  3. filtrationwere filtered
  4. dissolutiondissolved in dichloromethane
  5. additionby adding aqueous NaOH solution
  6. customThe dichloromethane layer was separated
  7. dry with materialdried over anhydrous sodium sulfate
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-f1e0700e0506480cb14d82d08c75fb9f
Source dataset
uspto-grants-1997_11
Patent number
US05686458

Reaction notes

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