Hydrochloric Acid → HCID 24966893, compound

HRID 1945474Notes

Reaction equation

HRID 1945474 reaction equation
C[O:2][C:3]([C:5]1[CH:25]=[CH:24][C:8]2[N:9]=[C:10]([CH2:12][O:13][C:14]3[CH:19]=[CH:18][C:17]([C:20]([CH3:23])([CH3:22])[CH3:21])=[CH:16][CH:15]=3)[O:11][C:7]=2[CH:6]=1)=[O:4].[Br-].[Al+3].[Br-].[Br-].O.Cl>CSC.ClCCl>[C:20]([C:17]1[CH:18]=[CH:19][C:14]([O:13][CH2:12][C:10]2[O:11][C:7]3[CH:6]=[C:5]([C:3]([OH:4])=[O:2])[CH:25]=[CH:24][C:8]=3[N:9]=2)=[CH:15][CH:16]=1)([CH3:23])([CH3:21])[CH3:22]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 166749BromhydrolHCID 24966185HCID 24966185, compound

Product 1

HCID 24966893HCID 24966893, compoundYield 77.7%

Reagents, catalysts & solvents 2

HCID 1068Dimethyl SulfideSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-(4-tert-butyl-phenoxymethyl)-benzoxazole-6-carboxylic acid methyl ester (67.8 mg, 0.20 mmol) in dimethyl sulfide (3 ml) and dichloromethane (3 ml) was added aluminum bromide (533.4 g, 2.0 mmol). The reaction mixture was stirred at room temperature for 2.5 h, after which water and 10% HCl were added. After stirring at room temperature for 1 h, the mixture was partitioned between ethyl acetate and water. The organic phase was washed with brine, dried (MgSO4 anh), and concentrated. The residue was purified by silica gel flash column chromatography (n-Hexane:EtoAc:MeOH=6:3:1) to give 2-(4-tert-butyl-phenoxymethyl)-benzoxazole-6-carboxylic acid as a white solid (50.5 mg, 77.7% yield).

Workup

  1. stirringAfter stirring at room temperature for 1 h
  2. customthe mixture was partitioned between ethyl acetate and water
  3. washThe organic phase was washed with brine
  4. dry with materialdried (MgSO4 anh)
  5. concentrationconcentrated
  6. customThe residue was purified by silica gel flash column chromatography (n-Hexane:EtoAc:MeOH=6:3:1)

Sources & evidence

ORD record
ord-5dbbc94e939545e6ae888947d54beefd
Source dataset
uspto-grants-2013_03
Patent number
US08394799B2

Reaction notes

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