Water → HCID 23025907, compound

HRID 1437485Notes

Reaction equation

HRID 1437485 reaction equation
[Br:1][C:2]1[CH:25]=[CH:24][C:5]2[N:6]=[C:7]([C:9]3[CH:10]=[C:11]([CH:21]=[CH:22][CH:23]=3)[O:12][CH2:13][C:14]([O:16]C(C)(C)C)=[O:15])[O:8][C:4]=2[CH:3]=1.Cl.C(OCC)(=O)C.O>O1CCCC1>[Br:1][C:2]1[CH:25]=[CH:24][C:5]2[N:6]=[C:7]([C:9]3[CH:10]=[C:11]([CH:21]=[CH:22][CH:23]=3)[O:12][CH2:13][C:14]([OH:16])=[O:15])[O:8][C:4]=2[CH:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 21866389Hydrogen chloride-ethyl acetateHCID 57941024HCID 57941024, compound

Product 1

HCID 23025907HCID 23025907, compoundYield 66.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of tert-butyl [3-(6-bromobenzoxazol-2-yl)phenoxy]acetate (Compound of Example 279) (2.22 g) in tetrahydrofuran (10 ml) was added 4 N hydrochloric acid-ethyl acetate (50 ml), and the mixture was stirred at room temperature for 2 hours. The reaction mixture was poured into water and extracted with ethyl acetate-tetrahydrofuran (3:1, v/v). The organic layer was washed with water and dried over MgSO4. The solvent was distilled off under reduced pressure, and the resulting crystals were collected by filtration to obtain [3-(6-bromobenzoxazol-2-yl)phenoxy]acetic acid (1.27 g, 66%). The crystals were recrystallized from tetrahydrofuran-ethyl acetate.

Workup

  1. extractionextracted with ethyl acetate-tetrahydrofuran (3:1
  2. washThe organic layer was washed with water
  3. dry with materialdried over MgSO4
  4. distillationThe solvent was distilled off under reduced pressure
  5. filtrationthe resulting crystals were collected by filtration

Sources & evidence

ORD record
ord-dc2b4110d50e44dab329d563604788b0
Source dataset
uspto-grants-2009_11
Patent number
US07622479B2

Reaction notes

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