Sodium Carbonate → (R)-1-(2-phenyl-4-chlorophenyl)-2,2,2-trifluoroethanol

HRID 1499117Notes

Reaction equation

HRID 1499117 reaction equation
Br[C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C@@H:9]([OH:14])[C:10]([F:13])([F:12])[F:11].[C:15]1(B(O)O)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.C([O-])([O-])=O.[Na+].[Na+]>O1CCOCC1>[Cl:8][C:6]1[CH:5]=[CH:4][C:3]([C@@H:9]([OH:14])[C:10]([F:13])([F:12])[F:11])=[C:2]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH:7]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 66827Phenylboronic AcidHCID 66742830(R)-1-(2-bromo-4-chlorophenyl)-2,2,2-trifluoroethanol

Product 1

HCID 117951866(R)-1-(2-phenyl-4-chlorophenyl)-2,2,2-trifluoroethanol

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of (R)-1-(2-bromo-4-chlorophenyl)-2,2,2-trifluoroethanol (300 mg, 1.1 mmol) in dioxane (12 mL) was added phenyl boronic acid (185 mg, 1.5 mmol), Pd2(dppf)Cl2 (35 mg, 0.07 mmol) and Na2CO3 (3 mL, 2.0 M, aq). The reaction was heated to 90° C. for 2 h, then cooled to RT, and concentrated in vacuo. The residue was taken up in CH2Cl2, washed with brine, and extracted with CH2Cl2. The combined organic layers were dried over Na2SO4. Purification by normal phase silica gel column (EtOAc/hexanes) to provide a white solid.

Workup

  1. temperaturecooled to RT
  2. concentrationconcentrated in vacuo
  3. washwashed with brine
  4. extractionextracted with CH2Cl2
  5. dry with materialThe combined organic layers were dried over Na2SO4
  6. customPurification by normal phase silica gel column (EtOAc/hexanes)
  7. customto provide a white solid

Sources & evidence

ORD record
ord-5dbd0b0a4fe9482483cbe18f0f1850c6
Source dataset
uspto-grants-2015_12
Patent number
US09199994B2

Reaction notes

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