Chlorosuccinimide → HCID 46218813, compound

HRID 386849Notes

Reaction equation

HRID 386849 reaction equation
[Cl:1]N1C(=O)CCC1=O.[O:9]1[CH2:14][CH2:13][CH:12]([C:15]2[CH:20]=[CH:19][C:18]([OH:21])=[CH:17][C:16]=2[OH:22])[CH2:11][CH2:10]1>ClCCl>[Cl:1][C:19]1[CH:20]=[C:15]([CH:12]2[CH2:11][CH2:10][O:9][CH2:14][CH2:13]2)[C:16]([OH:22])=[CH:17][C:18]=1[OH:21]

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 462078331228321-01-4

Product 1

HCID 46218813HCID 46218813, compoundYield 17%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2.4 g of N-chlorosuccinimide are added to a solution of 2 g of 4-(tetrahydropyran-4-yl)benzene-1,3-diol (Example 1) in 30 ml of dichloromethane at 0° C. The reaction mixture is stirred at ambient temperature for 16 hours. The reaction mixture is extracted with dichloromethane and then washed with water. The organic phases are combined and then dried over sodium sulphate. The residue is chromatographed on silica gel (75/25 heptane/ethyl acetate). 400 mg of 4-chloro-6-(tetrahydropyran-4-yl)benzene-1,3-diol are obtained. Yield=17%.

Workup

  1. extractionThe reaction mixture is extracted with dichloromethane
  2. washwashed with water
  3. dry with materialdried over sodium sulphate
  4. customThe residue is chromatographed on silica gel (75/25 heptane/ethyl acetate)

Sources & evidence

ORD record
ord-927ece7fa95d4b21af35b319ba63e514
Source dataset
uspto-grants-2013_02
Patent number
US08372879B2

Reaction notes

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