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

HRID 1007348Notes

Reaction equation

HRID 1007348 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-4c400f0bdc5c494b8ac9dc04047eb743
Source dataset
uspto-grants-2004_09
Patent number
US06794403B2

Reaction notes

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