Boron tribromide → HCID 19040960, compound

HRID 1683817Notes

Reaction equation

HRID 1683817 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-5305a1747cdd40e8bac92e2c3a5d0562
Source dataset
uspto-grants-1997_06
Patent number
US05639768

Reaction notes

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