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

HRID 1844622Notes

Reaction equation

HRID 1844622 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-f68d9d58a2af4c3a8dcf4394225b980c
Source dataset
uspto-grants-2015_02
Patent number
US08946449B2

Reaction notes

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