Water → 4-Chloro-5-hydroxy-1(3H)-isobenzofuranone

HRID 1186945Notes

Reaction equation

HRID 1186945 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[C:4]([Cl:9])[C:3]=1[CH2:10][OH:11].C([Cu])#N.CN([CH:18]=[O:19])C.O>C(Cl)Cl>[Cl:9][C:4]1[C:3]2[CH2:10][O:11][C:18](=[O:19])[C:2]=2[CH:7]=[CH:6][C:5]=1[OH:8]

Participants

6

Reactant 4

HCID 962WaterHCID 6228DimethylformamideHCID 66643855HCID 66643855, compoundHCID 178418546HCID 178418546, compound

Product 1

HCID 666440034-Chloro-5-hydroxy-1(3H)-isobenzofuranone

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
145 °C

Procedure

To a flask charged with 4-bromo-2-chloro-3-(hydroxymethyl)phenol (2.44 g, 10.3 mmol) and a stir bar was added CuCN (2.76 g, 30.8 mmol) and DMF (25 mL). The flask was fitted with a condenser and purged three times with Nitrogen. The solution was then heated to 145° C. for 2 hours. At that point, water (0.555 mL, 30.8 mmol) was added to the reaction via a syringe, and the reaction was kept at 100° C. for another 24 hours. The reaction was cooled to RT, diluted with DCM (100 mL), and filtered through a pad of celite to remove the solids. The filtrate was washed with saturated NH4OAc, dried over sodium sulfate, concentrated and purified by silica gel flash chromatography. 4-Chloro-5-hydroxy-2-benzofuran-1(3H)-one was collected after removal of solvents. 1H-NMR (500 MHz, CDCl3) δ ppm 9.13 (broad, 1H), 7.68 (d, J=8.5 Hz, 1H), 7.19 (d, J=8.5 Hz, 1H), 5.23 (s, 2H).

Workup

  1. customThe flask was fitted with a condenser
  2. custompurged three times with Nitrogen
  3. temperatureThe reaction was cooled to RT
  4. filtrationfiltered through a pad of celite
  5. customto remove the solids
  6. washThe filtrate was washed with saturated NH4OAc
  7. dry with materialdried over sodium sulfate
  8. concentrationconcentrated
  9. custompurified by silica gel flash chromatography
  10. custom4-Chloro-5-hydroxy-2-benzofuran-1(3H)-one was collected
  11. customafter removal of solvents

Sources & evidence

ORD record
ord-201dddde3ac84d3292129bfc927fb584
Source dataset
uspto-grants-2014_03
Patent number
US08673920B2

Reaction notes

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