Acetic Anhydride → 4-[5-(Acetyloxy)-7-bromo-1,3-benzoxazol-2-yl]-2-fluorophenyl acetate

HRID 491735Notes

Reaction equation

HRID 491735 reaction equation
[C:1](OC(=O)C)(=[O:3])[CH3:2].[Br:8][C:9]1[C:17]2[O:16][C:15]([C:18]3[CH:23]=[CH:22][C:21]([OH:24])=[C:20]([F:25])[CH:19]=3)=[N:14][C:13]=2[CH:12]=[C:11]([OH:26])[CH:10]=1.[O:27]1CCO[CH2:29][CH2:28]1>CN(C)C1C=CN=CC=1.O>[C:1]([O:24][C:21]1[CH:22]=[CH:23][C:18]([C:15]2[O:16][C:17]3[C:9]([Br:8])=[CH:10][C:11]([O:26][C:28](=[O:27])[CH3:29])=[CH:12][C:13]=3[N:14]=2)=[CH:19][C:20]=1[F:25])(=[O:3])[CH3:2]

Participants

6

Reactant 3

HCID 7918Acetic AnhydrideHCID 312751,4-DioxaneHCID 1354573257-Bromo-2-(3-fluoro-4-hydroxyphenyl)benzo[d]oxazol-5-ol

Product 1

HCID 219073714-[5-(Acetyloxy)-7-bromo-1,3-benzoxazol-2-yl]-2-fluorophenyl acetateYield 56%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 962WaterSolvent

Procedure

Acetic anhydride (1.0 mL, 9.95 mmol) was added into a cold (0° C.) solution of 7-bromo-2-(3-fluoro-4-hydroxyphenyl)-1,3-benzoxazol-5-ol (1.24 g, 3.8 mmol), N,N-dimethylpyridin-4-amine (1.1 g, 9.18 mmol) and 1,4-dioxane (13 mL). The reaction mixture was allowed to warm up to room temperature and stirred for 20 h. Water (50 mL) was added to the reaction mixture extracted with EtOAc and dried over MgSO4. Evaporation and crystallization from EtOAc/hexane gave an off-white solid (0.87 g, 56% yield); MS m/e 408 (M+H)+.

Workup

  1. extractionextracted with EtOAc
  2. dry with materialdried over MgSO4
  3. customEvaporation and crystallization from EtOAc/hexane

Sources & evidence

ORD record
ord-6463f1ec85ef428396c930b445ec4920
Source dataset
uspto-grants-2009_05
Patent number
US07531564B2

Reaction notes

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