Benzyl Bromide → HCID 22139411, compound

HRID 1825789Notes

Reaction equation

HRID 1825789 reaction equation
C([O-])([O-])=O.[K+].[K+].[F:7][C:8]1[C:21]2[C:20](=[O:22])[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[S:13][C:12]=2[C:11]([OH:23])=[CH:10][CH:9]=1.[CH2:24](Br)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>CO>[CH2:24]([O:23][C:11]1[C:12]2[S:13][C:14]3[C:19](=[CH:18][CH:17]=[CH:16][CH:15]=3)[C:20](=[O:22])[C:21]=2[C:8]([F:7])=[CH:9][CH:10]=1)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 136150131-Fluoro-4-hydroxy-9H-thioxanthen-9-one

Product 1

HCID 22139411HCID 22139411, compoundYield 66.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

K2CO3 (21.0 g, 150 mmol) was added to a stirred suspension of 1-Fluoro-4-hydroxy-thioxanthen-9-one (18.47 g, 75.0 mmol) in methanol (100 mL) followed by benzylbromide (16 mL, 75.0 mmol) which was added in slow stream via syringe. The resulting mixture was then heated to reflux for 90 minutes and then cooled to room temperature before it was poured onto crushed ice (0.5 L). The resulting precipitate was filtered off and dried (P2O5) to give the title compound as a yellow solid (16.7 g, 66.1%) m/z (LC-MS, ESP): 337 [M+H]+, R/T=5.22 mins

Workup

  1. additionwas added in slow stream via syringe
  2. temperatureThe resulting mixture was then heated
  3. temperatureto reflux for 90 minutes
  4. additionwas poured
  5. filtrationThe resulting precipitate was filtered off
  6. dry with materialdried (P2O5)

Sources & evidence

ORD record
ord-59073f5fc6914871940a3416d3f51b3e
Source dataset
uspto-grants-2006_05
Patent number
US07049313B2

Reaction notes

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