Boron tribromide → Emd638683

HRID 1037747Notes

Reaction equation

HRID 1037747 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:9]([OH:27])[C:10]([NH:12][NH:13][C:14](=[O:26])[C:15]2[CH:20]=[CH:19][C:18]([O:21]C)=[C:17]([CH3:23])[C:16]=2[CH2:24][CH3:25])=[O:11])[CH:5]=[C:6]([F:8])[CH:7]=1.B(Br)(Br)Br>ClCCl>[F:1][C:2]1[CH:3]=[C:4]([CH:9]([OH:27])[C:10]([NH:12][NH:13][C:14](=[O:26])[C:15]2[CH:20]=[CH:19][C:18]([OH:21])=[C:17]([CH3:23])[C:16]=2[CH2:24][CH3:25])=[O:11])[CH:5]=[C:6]([F:8])[CH:7]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 69810311N'-(2-(3,5-Difluorophenyl)-2-hydroxyacetyl)-2-ethyl-4-methoxy-3-methylbenzohydrazide

Product 1

HCID 44182398Emd638683Yield 47.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

70.0 g of N′-[2-(3,5-difluorophenyl)-2-hydroxyacetyl]-2-ethyl-4-methoxy-3-methylbenzohydrazide (A1) are suspended in 350 ml of dichloromethane. 105 ml of boron tribromide are then added dropwise. The reaction mixture is stirred at room temperature for 3 hours. The resultant solution is subsequently carefully decanted into one litre of ice-water. The aqueous phase is extracted twice with 500 ml of ethyl acetate. The combined organic phases are then extracted once with 300 ml of water, dried over sodium sulfate and subsequently filtered. The filtrate is concentrated in vacuo. The resultant residue is, then recrystallised from 500 ml of acetonitrile using activated carbon, giving 32.2 g of the title compound as colourless solid having a melting point of 187.4° C. (MS: 365 (MH+), TLC: Rf=0.29 (cyclohexane/methyl tert-butyl ether 1:4, parts by volume).

Workup

  1. customThe resultant solution is subsequently carefully decanted into one litre of ice-water
  2. extractionThe aqueous phase is extracted twice with 500 ml of ethyl acetate
  3. extractionThe combined organic phases are then extracted once with 300 ml of water
  4. dry with materialdried over sodium sulfate
  5. filtrationsubsequently filtered
  6. concentrationThe filtrate is concentrated in vacuo
  7. customrecrystallised from 500 ml of acetonitrile using activated carbon

Sources & evidence

ORD record
ord-b8d4f328a62b49dea2cff968dac39468
Source dataset
uspto-grants-2013_10
Patent number
US08546613B2

Reaction notes

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