Trifluoroacetic acid → 2-(Dicyclohexylphosphino)benzenesulfonic acid

HRID 337702

Reaction equation

HRID 337702 reaction equation
C([Li])CCC.[C:6]1([S:12]([OH:15])(=[O:14])=[O:13])[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.Cl[P:17]([CH:24]1[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]1)[CH:18]1[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]1.FC(F)(F)C(O)=O>O1CCCC1>[CH:24]1([P:17]([CH:18]2[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23]2)[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=2[S:12]([OH:15])(=[O:14])=[O:13])[CH2:25][CH2:26][CH2:27][CH2:28][CH2:29]1

Participants

6

Reactant 4

HCID 6422Trifluoroacetic acidHCID 7371Benzenesulfonic AcidHCID 2734135ChlorodicyclohexylphosphineHCID 178418339Butyllithium

Product 1

HCID 190091372-(Dicyclohexylphosphino)benzenesulfonic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

n-Butyllithium (manufactured by Kanto Chemical Co., Inc., 1.65 M hexane solution, 5.1 ml, 8.4 mmol) was added to a tetrahydrofuran (THF) solution (20 ml) of benzenesulfonic acid (manufactured by Tokyo Chemical Industry Co., Ltd., 0.66 g, 4.2 mmol) at 0° C. under argon atmosphere and the mixture was stirred for 2.5 hours at room temperature. After cooling the reaction container to −78° C., chlorodicyclohexylphosphine (manufactured by Sigma-Aldrich, 0.89 mg, 3.8 mmol) was added thereto at −78° C. and stirred for 24 hours at room temperature. After ceasing the reaction with trifluoroacetic acid (manufactured by Tokyo Chemical Industry Co., Ltd., 0.50 M THF solution, 8.4 ml, 4.2 mmol), the precipitate formed was collected by filtration and dried under reduced pressure to obtain 2-(dicyclohexylphosphino)benzenesulfonic acid (compound 1a). The yield was 0.66 g (85%).

Workup

  1. temperatureAfter cooling the reaction container to −78° C.
  2. stirringat −78° C. and stirred for 24 hours at room temperature
  3. customthe precipitate formed
  4. filtrationwas collected by filtration
  5. customdried under reduced pressure

Sources & evidence

ORD record
ord-72a42cbe9b3a44939e5eac43ee92e958
Source dataset
uspto-grants-2014_11
Patent number
US08889805B2

Linked notes

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