Lithium Bromide → 3-Bromo-1,1-bis(4-fluorophenyl)propane

HRID 2190305Notes

Reaction equation

HRID 2190305 reaction equation
CC1C=CC(S(O[CH2:12][CH2:13][CH:14]([C:22]2[CH:27]=[CH:26][C:25]([F:28])=[CH:24][CH:23]=2)[C:15]2[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=2)(=O)=O)=CC=1.[Br-:29].[Li+]>CC(C)=O.CCOCC>[Br:29][CH2:12][CH2:13][CH:14]([C:22]1[CH:27]=[CH:26][C:25]([F:28])=[CH:24][CH:23]=1)[C:15]1[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=1

Participants

5

Reactant 2

HCID 82050Lithium BromideHCID 222258963,3-Bis(4-fluorophenyl)propyl 4-methylbenzenesulfonate

Product 1

HCID 138832773-Bromo-1,1-bis(4-fluorophenyl)propane

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 3283Diethyl EtherSolvent

Procedure

To a solution of 3,3-bis(4-fluorophenyl)propyl 4-methylbenzenesulfonate, prepared in the previous step, in acetone (100 mL) was added lithium bromide (17.83 g, 205 mmol). The reaction mixture was stirred at room temperature for 17 h, and concentrated. The crude reaction mixture was diluted with Et2O, washed with water (2×), brine (1×), dried over MgSO4, filtered, and concentrated. Purification by flash column chromatography on silica gel (eluted with 0% to 20% EtOAc in hexanes) gave 3-bromo-1,1-bis(4-fluorophenyl)propane.

Workup

  1. concentrationconcentrated
  2. customThe crude reaction mixture
  3. washwashed with water (2×), brine (1×)
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customPurification by flash column chromatography on silica gel (eluted with 0% to 20% EtOAc in hexanes)

Sources & evidence

ORD record
ord-8c6d84cdea1443fa845c51efbc62ebdc
Source dataset
uspto-grants-2012_12
Patent number
US08324396B2

Reaction notes

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