Diboron → HCID 21487801, compound

HRID 1414535Notes

Reaction equation

HRID 1414535 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[C:6](=O)[C:7]3[C:12]([S:13][C:14]=2[CH:15]=1)=[C:11]([O:16][CH3:17])[CH:10]=[CH:9][CH:8]=3.B#B>O1CCCC1.O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[CH2:6][C:7]3[C:12]([S:13][C:14]=2[CH:15]=1)=[C:11]([O:16][CH3:17])[CH:10]=[CH:9][CH:8]=3

Participants

5

Reactant 2

HCID 6328200DiboronHCID 21487822HCID 21487822, compound

Product 1

HCID 21487801HCID 21487801, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

A stirred suspension of 3-chloro-5-methoxythioxanth-9-one (13.8 g.) in dry tetrahydrofuran (140 ml.) is treated dropwise with a solution of diborane in tetrahydrofuran (1M, 40 ml.) at ambient temperature and in an atmosphere of argon. The mixture is heated at reflux for 1.25 hours, cooled, diluted carefully with water and extracted with ether (× 3). The combined ether extracts are washed with brine, dried over MgSO4 and then evaporated, to give 3-chloro-5-methoxythioxanthene, m.p. 72°-74° C. on recrystallisation from methanol.

Workup

  1. temperatureThe mixture is heated
  2. temperatureat reflux for 1.25 hours
  3. temperaturecooled
  4. extractionextracted with ether (× 3)
  5. washThe combined ether extracts are washed with brine
  6. dry with materialdried over MgSO4
  7. customevaporated

Sources & evidence

ORD record
ord-994ffdba3f1b457ba1bf9d9aca8fb548
Source dataset
uspto-grants-1977_01
Patent number
US04001418

Reaction notes

Loading…