Boron tribromide → HCID 19040960, compound

HRID 2399948Notes

Reaction equation

HRID 2399948 reaction equation
C[O:2][C:3]1[CH:20]=[C:19]([O:21]C)[CH:18]=[CH:17][C:4]=1[C:5]([N:7]([CH:14]([CH3:16])[CH3:15])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)=[O:6].B(Br)(Br)Br>ClCCl>[OH:2][C:3]1[CH:20]=[C:19]([OH:21])[CH:18]=[CH:17][C:4]=1[C:5]([N:7]([CH:14]([CH3:16])[CH3:15])[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)=[O:6]

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 19040985HCID 19040985, compound

Product 1

HCID 19040960HCID 19040960, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A stirred solution of 2,4-dimethoxy-N-(1-methylethyl)-N-phenylbenzamide (2.4 g, 8.03 mmol) in 10 ml of dichloromethane at 0° C. was treated with 1N boron tribromide (33.2 mL, 33.2 mmol) and stirred at room temperature for 1 hour. The reaction is poured in to the ice water. After stirring for 15 minutes, the reaction was partitioned between ethyl acetate and brine, dried over magnesium sulfate and concentrated in vacuo to afford yellow foam. This material is purified by chromatography on silica gel (70 g) with 3-5% methanol/dichloromethane as the eluent to afford 2,4-dihydroxy-N-(1-methylethyl)-N-phenylbenzamide as colorless foam.

Workup

  1. stirringAfter stirring for 15 minutes
  2. customthe reaction was partitioned between ethyl acetate and brine
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated in vacuo
  5. customto afford yellow foam
  6. customThis material is purified by chromatography on silica gel (70 g) with 3-5% methanol/dichloromethane as the eluent

Sources & evidence

ORD record
ord-07b264b656a64eaf925a6e38843ca29b
Source dataset
uspto-grants-1995_09
Patent number
US05451700

Reaction notes

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