4-Fluoro-2-hydroxyphenacyl bromide → 6-Fluoro-2,3-dihydro-1-benzofuran-3-one

HRID 2377302Notes

Reaction equation

HRID 2377302 reaction equation
Br[CH2:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([F:11])=[CH:7][C:6]=1[OH:12])=[O:4]>CN(C=O)C.O>[F:11][C:8]1[CH:9]=[CH:10][C:5]2[C:3](=[O:4])[CH2:2][O:12][C:6]=2[CH:7]=1

Participants

4

Reactant 1

HCID 269860714-Fluoro-2-hydroxyphenacyl bromide

Product 1

HCID 183543126-Fluoro-2,3-dihydro-1-benzofuran-3-oneYield 76.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

CsCO3 (5.36 g) was added in portions over 10 min to an ice cold solution of Example 1109A (3.2 g) in DMF (140 mL). The resulting mixture was stirred for 30 min then diluted with water and extracted with ether (3×). the combined extracts were dried (Na2SO4), and concentrated to give 1.6 g of the title compound. MS ESI(−) m/e 151.1 (M−H)−.

Workup

  1. extractionextracted with ether (3×)
  2. dry with materialthe combined extracts were dried (Na2SO4)
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-5017a460639f48b887a99440acc67f77
Source dataset
uspto-grants-2008_12
Patent number
US07468371B2

Reaction notes

Loading…