Boron tribromide → 2-[4-(4-Hydroxy-3-isopropylbenzyl)-3,5-dimethylanilino]-2-oxoacetic acid

HRID 392893Notes

Reaction equation

HRID 392893 reaction equation
[CH:1]([C:4]1[CH:5]=[C:6]([CH:24]=[CH:25][C:26]=1[O:27]C)[CH2:7][C:8]1[C:21]([CH3:22])=[CH:20][C:11]([NH:12][C:13](=[O:19])[C:14]([O:16]CC)=[O:15])=[CH:10][C:9]=1[CH3:23])([CH3:3])[CH3:2].B(Br)(Br)Br>ClCCl>[OH:27][C:26]1[CH:25]=[CH:24][C:6]([CH2:7][C:8]2[C:9]([CH3:23])=[CH:10][C:11]([NH:12][C:13](=[O:19])[C:14]([OH:16])=[O:15])=[CH:20][C:21]=2[CH3:22])=[CH:5][C:4]=1[CH:1]([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 10110509Ethyl 2-[4-(3-isopropyl-4-methoxybenzyl)-3,5-dimethylanilino]-2-oxoacetate

Product 1

HCID 99498772-[4-(4-Hydroxy-3-isopropylbenzyl)-3,5-dimethylanilino]-2-oxoacetic acidYield 99.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

128 mg (0.33 mmol) of ethyl 2-[4-(3-isopropyl-4-methoxybenzyl)-3,5-dimethyl-anilino]-2-oxoacetate (Example 1) in 5 ml of dichloromethane at −78° C. under argon are treated dropwise with 167 mg (0.66 mmol) of boron tribromide. The reaction mixture is stirred at room temperature for 2.5 hours. It is poured into buffer of pH 7, the phases are separated, the aqueous phase is acidified with buffer of pH 4 and, after extraction with dichloromethane, the organic phases are combined. The solution is dried over sodium sulphate and the solvent is removed in vacuo. 112 mg (98%) of 2-[4-(4-hydroxy-3-isopropylbenzyl)-3,5-dimethylanilino]-2-oxoacetic acid are obtained.

Workup

  1. additionIt is poured into buffer of pH 7
  2. customthe phases are separated
  3. extractionafter extraction with dichloromethane
  4. dry with materialThe solution is dried over sodium sulphate
  5. customthe solvent is removed in vacuo

Sources & evidence

ORD record
ord-695b0d56d4174bbbbd54b9592b224090
Source dataset
uspto-grants-2004_10
Patent number
US06803480B2

Reaction notes

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