1-Bromo-3-chloropropane → HCID 69085462, compound

HRID 1056501Notes

Reaction equation

HRID 1056501 reaction equation
[Na].[Cl:2][C:3]1[C:16]2[C:15](=[O:17])[C:14]3[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=3)[S:8][C:7]=2[C:6]([OH:18])=[CH:5][CH:4]=1.Br[CH2:20][CH2:21][CH2:22][Cl:23]>C(O)(C)C.O>[Cl:2][C:3]1[C:16]2[C:15](=[O:17])[C:14]3[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=3)[S:8][C:7]=2[C:6]([O:18][CH2:20][CH2:21][CH2:22][Cl:23])=[CH:5][CH:4]=1

Participants

6

Reactant 3

HCID 80061-Bromo-3-chloropropaneHCID 28259241-Chloro-4-hydroxythioxanthoneHCID 5360545Sodium

Product 1

HCID 69085462HCID 69085462, compoundYield 72%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3776IsopropanolSolvent2×

Procedure

A 500 mL flask was charged with the sodium salt of 1-chloro-4-hydroxy-9H-thioxanthen-9-one (28.5 g; 0.100 mol), 1-bromo-3-chloropropane (17.4 g; 0.111 mol) and isopropyl alcohol (280 mL). The turbid reaction mixture was refluxed for 24 h. The hot solution was diluted with isopropyl alcohol (130 mL), drowned out in water (1400 mL) and the resulting suspension was extracted with dichloromethane (3×250 mL). The organic phase was separated, dried (MgSO4), filtered and solvent removed in vacuo to give 1-chloro-4-(3-chloropropoxy)-9H-thioxanthen-9-one (24.4 g; 72% yield).

Workup

  1. customThe turbid reaction mixture
  2. temperaturewas refluxed for 24 h
  3. extractionthe resulting suspension was extracted with dichloromethane (3×250 mL)
  4. customThe organic phase was separated
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. customsolvent removed in vacuo

Sources & evidence

ORD record
ord-a0281ba58f504f59aec0553acbb4e664
Source dataset
uspto-grants-2016_07
Patent number
US09399633B2

Reaction notes

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