Water → HCID 86683466, compound

HRID 515803Notes

Reaction equation

HRID 515803 reaction equation
B(Br)(Br)Br.C([O:12][CH2:13][CH2:14][CH2:15][CH2:16][S:17][CH2:18][CH2:19][CH2:20][C:21]([F:27])([F:26])[C:22]([F:25])([F:24])[F:23])C1C=CC=CC=1.O>C(Cl)Cl>[F:27][C:21]([F:26])([C:22]([F:23])([F:24])[F:25])[CH2:20][CH2:19][CH2:18][S:17][CH2:16][CH2:15][CH2:14][CH2:13][OH:12]

Participants

5

Reactant 3

HCID 962WaterHCID 25134Boron tribromideHCID 86683467HCID 86683467, compound

Product 1

HCID 86683466HCID 86683466, compoundYield 67.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-78 °C

Procedure

BBr3 (1M in DCM, 2.9 mL, 2.9 mmol) was added dropwise to a solution of (4-(benzyloxy)butyl)(4,4,5,5,5-pentafluoropentyl)sulfane (340 mg, 0.95 mmol) in DCM (5 mL) cooled to −78° C. The temperature was allowed to warm up to room temperature and the mixture was stirred for 18 h. Water was slowly added and the reaction mixture was stirred for 10 min. The two layers were separated and the aqueous layer was extracted with DCM (3×). The organics were combined, dried over sodium sulfate, and evaporated to dryness. The residue was purified by column chromatography on silica gel eluting with 50 to 100% EtOAc/hexanes to afford 171 mg of 4-((4,4,5,5,5-pentafluoropentyl)thio)butan-1-ol as a colorless oil.

Workup

  1. temperatureto warm up to room temperature
  2. stirringthe reaction mixture was stirred for 10 min
  3. customThe two layers were separated
  4. extractionthe aqueous layer was extracted with DCM (3×)
  5. dry with materialdried over sodium sulfate
  6. customevaporated to dryness
  7. customThe residue was purified by column chromatography on silica gel eluting with 50 to 100% EtOAc/hexanes

Sources & evidence

ORD record
ord-7b5ec2e035da414fae904b46a695ac72
Source dataset
uspto-grants-2015_08
Patent number
US09108944B2

Reaction notes

Loading…