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

HRID 1848520Notes

Reaction equation

HRID 1848520 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 to afford title compound.

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

Sources & evidence

ORD record
ord-0093c5c0caa64a09aa9b6416cb5302bd
Source dataset
uspto-grants-2015_02
Patent number
US08952166B2

Reaction notes

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