Butanethiol → HCID 90414055, compound

HRID 1746041Notes

Reaction equation

HRID 1746041 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[OH:9].C(=O)([O-])[O-].[K+].[K+].Br[C:17]([F:23])([F:22])[C:18]([F:21])([F:20])[Br:19].C(S)CCC.[OH-].[Na+]>CN(C)C=O>[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[O:9][C:17]([F:23])([F:22])[C:18]([Br:19])([F:21])[F:20]

Participants

7

Reactant 5

HCID 8012ButanethiolHCID 11430Potassium CarbonateHCID 14798Sodium HydroxideHCID 313011,2-Dibromo-1,1,2,2-tetrafluoroethaneHCID 27792842-BROMO-6-FLUOROPHENOL

Product 1

HCID 90414055HCID 90414055, compoundYield 76.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

2-Bromo-6-fluorophenol (10.2 g, 53 mmol), potassium carbonate (7.3 g, 53 mmol), 1,2-dibromo-tetrafluoroethane (21 g, 80 mmol) and 1-butanethiol (1.1 g, 12 mmol) were combined in dry N,N-dimethylformamide (75 mL) and heated to 50° C. in a stirred pressure reactor. After cooling, the contents were mixed with 1.0 M sodium hydroxide (NaOH; 100 mL) and extracted three times with diethyl ether (80 mL portions). The combined extracts were washed with water (15 mL), 2.0 M NaOH (45 mL), dried (Na2SO4) and concentrated by rotary evaporation. The material was purified by silica gel chromatography eluting with hexane to afford the title compound as a clear liquid (15 g, 76%): 1H NMR (400 MHz, CDCl3) δ 7.48-7.39 (m, 1H), 7.22-7.14 (m, 2H); EIMS m/z 368.

Workup

  1. temperatureAfter cooling
  2. extractionextracted three times with diethyl ether (80 mL portions)
  3. washThe combined extracts were washed with water (15 mL), 2.0 M NaOH (45 mL)
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated by rotary evaporation
  6. customThe material was purified by silica gel chromatography
  7. washeluting with hexane

Sources & evidence

ORD record
ord-abcfd28db41d491a8c69383a55980740
Source dataset
uspto-grants-2015_10
Patent number
US09149038B2

Reaction notes

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