Water → 5-phenyl-5H-dibenzo[b,d]thiophenium 3-hydroxyadamantane-acetoxy-1,1,2,2-tetrafluorobutane-1-sulfonate

HRID 1841853Notes

Reaction equation

HRID 1841853 reaction equation
[Br-].[C:2]1([S+:8]2[C:12]3[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=3[C:10]3[CH:17]=[CH:18][CH:19]=[CH:20][C:9]2=3)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH:21][C:22]12[CH2:31][CH:26]3[CH2:27][CH:28]([CH2:30][CH:24]([CH2:25]3)[CH2:23]1)[CH2:29]2.[C:32]([O:35][CH:36]([CH3:47])[C:37]([F:46])([F:45])[C:38]([F:44])([F:43])[S:39]([O-:42])(=[O:41])=[O:40])(=[O:34])[CH3:33].[Na].O>ClCCl>[OH:21][C:22]12[CH2:23][CH:24]3[CH2:30][CH:28]([CH2:27][C:26]([CH2:33][C:32]([O:35][CH:36]([CH3:47])[C:37]([F:46])([F:45])[C:38]([F:44])([F:43])[S:39]([O-:42])(=[O:41])=[O:40])=[O:34])([CH2:25]3)[CH2:31]1)[CH2:29]2.[C:2]1([S+:8]2[C:9]3[CH:20]=[CH:19][CH:18]=[CH:17][C:10]=3[C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]2=3)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 867124565-Phenyl-5H-dibenzo[b,d]thiophen-5-ium BromideHCID 1317324103-Hydroxyadamantane acetoxy-1,1,2,2-tetrafluorobutane-1-sulfonate sodium

Product 1

HCID 1317324095-phenyl-5H-dibenzo[b,d]thiophenium 3-hydroxyadamantane-acetoxy-1,1,2,2-tetrafluorobutane-1-sulfonateYield 99%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

5-phenyl-5H-dibenzo[b,d]thiophenium bromide (28.0 g, 82.04 mmol) and 3-hydroxyadamantane-acetoxy-1,1,2,2-tetrafluorobutane-1-sulfonate-sodium salt (35.68 g, 83.7 mmol) were dissolved in dichloromethane (500 mL) and water (500 mL) and stirred at r.t. for 16 h. The dichloromethane layer was separated and the aqueous phase washed with dichloromethane (3×300 mL). The combined organic layers were washed with water (4×500 mL), concentrated in vacuo and residual water removed via azeotrope with acetonitrile (2×350 mL) to afford the title compound (54.00 g, 99%) as a white solid. 1H NMR (500 MHz, (CD3)2CO) δ: 8.55 (d, J=8 Hz, 2H), 8.41 (d, J=8 Hz, 2H), 8.02 (dt, J=7.5, 0.5 Hz, 2H), 7.77-7.84 (m, 5H), 7.67 (t, J=7.5 Hz, 2H), 4.31 (t, J=6.5 Hz, 2H), 3.63 (s, 10H), 2.71 (tt, J=14, 6.5 Hz, 2H), 1.52-1.80 (m, 12H).

Workup

  1. customThe dichloromethane layer was separated
  2. washthe aqueous phase washed with dichloromethane (3×300 mL)
  3. washThe combined organic layers were washed with water (4×500 mL)
  4. concentrationconcentrated in vacuo and residual water
  5. customremoved via azeotrope with acetonitrile (2×350 mL)

Sources & evidence

ORD record
ord-7e3629f0375b4c91bc4c57b706ae2f1c
Source dataset
uspto-grants-2015_02
Patent number
US08945814B2

Reaction notes

Loading…