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Hydrochloric Acid → 2-(4-Adamantan-1-yl-phenoxymethyl)-benzoxazole-5-carboxylic acid

HRID 1945470
Notes
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Reaction equation

HRID 1945470 reaction equation
C[O:2][C:3]([C:5]1[CH:6]=[CH:7][C:8]2[O:12][C:11]([CH2:13][O:14][C:15]3[CH:20]=[CH:19][C:18]([C:21]45[CH2:30][CH:25]6[CH2:26][CH:27]([CH2:29][CH:23]([CH2:24]6)[CH2:22]4)[CH2:28]5)=[CH:17][CH:16]=3)=[N:10][C:9]=2[CH:31]=1)=[O:4].[Br-].[Al+3].[Br-].[Br-].O.Cl>CSC.ClCCl>[C:21]12([C:18]3[CH:19]=[CH:20][C:15]([O:14][CH2:13][C:11]4[O:12][C:8]5[CH:7]=[CH:6][C:5]([C:3]([OH:4])=[O:2])=[CH:31][C:9]=5[N:10]=4)=[CH:16][CH:17]=3)[CH2:28][CH:27]3[CH2:29][CH:23]([CH2:24][CH:25]([CH2:26]3)[CH2:30]1)[CH2:22]2
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 166749BromhydrolHCID 24812203HCID 24812203, compound

Product 1

HCID 249665342-(4-Adamantan-1-yl-phenoxymethyl)-benzoxazole-5-carboxylic acidYield 66%

Reagents, catalysts & solvents 2

HCID 1068
Dimethyl Sulfide
Solvent
HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-(4-adamantan-1-yl-phenoxymethyl)-benzoxazole-5-carboxylic acid methyl ester (100 mg, 0.24 mmol) in dimethyl sulfide (5 ml) and dichloromethane (5 ml) was added aluminum bromide (1.02 g, 3.84 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 (CH2Cl2:MeOH=4:1) to give 2-(4-adamantan-1-yl-phenoxymethyl)-benzoxazole-5-carboxylic acid as a white solid (63.8 mg, 66.0% 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 (CH2Cl2:MeOH=4:1)

Sources & evidence

ORD record
ord-b38082bd0ab241e3971552f101bbf1f3
Source dataset
uspto-grants-2013_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08394799B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes