Chloroform → (5-Fluoro-2,3-dihydro-1-benzofuran-2-yl)methanol

HRID 2069690Notes

Reaction equation

HRID 2069690 reaction equation
[CH2:1]([C:4]1[CH:9]=[C:8]([F:10])[CH:7]=[CH:6][C:5]=1[OH:11])[CH:2]=[CH2:3].ClC1C=C(C=CC=1)[C:16](OO)=[O:17].[CH:23]([Cl:26])(Cl)Cl>>[Cl:26][CH2:23][C:6]1[C:5]2[O:11][CH:2]([CH2:3][O:17][CH3:16])[CH2:1][C:4]=2[CH:9]=[C:8]([F:10])[CH:7]=1.[F:10][C:8]1[CH:7]=[CH:6][C:5]2[O:11][CH:2]([CH2:3][OH:17])[CH2:1][C:4]=2[CH:9]=1

Participants

5

Reactant 3

HCID 6212Chloroform2×HCID 70297m-Chloroperbenzoic acidHCID 113441122-Allyl-4-fluorophenol

Product 2

HCID 19886355(5-Fluoro-2,3-dihydro-1-benzofuran-2-yl)methanolYield 57.7%HCID 58566367HCID 58566367, compound

Conditions

Temperature
0 °C

Procedure

To an ice cold solution of 2-allyl-4-fluorophenol (853) (6.0 g, 36.2 mmol) in CHCl3 (180.0 mL) was added slowly the suspension of 77% 3-chloroperoxybenzoic acid (8.1 g, 36.2 mmol) in CHCl3 (36.2 mL). The resulting mixture was stirred at 0° C. for 2 hours, then washed with NaHCO3 (100 mL), water (2×100 mL), brine (100 mL) and dried over sodium sulfate, filtered and concentrated in vacuo. The residue was purified by flash chromatography on silica gel (30-40% EtOAc in hexanes) to provide the desired product (5-fluoro-2,3-dihydrobenzofuran-2-yl)methanol (854) (3.8 g, 57.7%) as a yellow oil.

Workup

  1. washwashed with NaHCO3 (100 mL), water (2×100 mL), brine (100 mL)
  2. dry with materialdried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by flash chromatography on silica gel (30-40% EtOAc in hexanes)

Sources & evidence

ORD record
ord-523293aa52024e369056d7a60157ff1e
Source dataset
uspto-grants-2012_10
Patent number
US08299117B2

Reaction notes

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