Hydrogen Bromide → HCID 18425768, compound

HRID 1280730Notes

Reaction equation

HRID 1280730 reaction equation
C1(C)C=CC(S([N:10]2[CH2:14][CH2:13][CH:12]([S:15][C:16]3[CH:21]=[CH:20][C:19]([OH:22])=[CH:18][CH:17]=3)[CH2:11]2)(=O)=O)=CC=1.C1(O)C=CC=CC=1.[BrH:31]>>[BrH:31].[NH:10]1[CH2:14][CH2:13][CH:12]([S:15][C:16]2[CH:21]=[CH:20][C:19]([OH:22])=[CH:18][CH:17]=2)[CH2:11]1

Participants

4

Reactant 3

HCID 260Hydrogen BromideHCID 996PhenolHCID 18425785HCID 18425785, compound

Product 1

HCID 18425768HCID 18425768, compoundYield 75%

Conditions

Temperature
100 °C

Procedure

(RS)-4-[1-(Toluene-4-sulfonyl)-pyrrolidin-3-ylsulfanyl]-phenol (1.9 g, 5.44 mmol) in phenol (5.1 g, 54.4 mmol) was treated with HBr (25 ml, 48%). After 4 hours stirring at 100° C., the reaction mixture was cooled to room temperature and quenched with H2O and CH2Cl2. The aqueous phase was washed with CH2Cl2 and concentrated to provide (RS)-4-(pyrrolidin-3-ylsulfanyl)-phenol hydrobromide (1.13 g, 75%) as a brown oil, MS: m/e=196.2 (M+H+). Following the general method of example 74, the compounds of example 75 to example 77 were prepared.

Workup

  1. temperaturethe reaction mixture was cooled to room temperature
  2. customquenched with H2O and CH2Cl2
  3. washThe aqueous phase was washed with CH2Cl2
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-f75945b65e9d4d1dac43de47ee348d63
Source dataset
uspto-grants-2002_09
Patent number
US06451819B2

Reaction notes

Loading…