(Diethylamino)sulfur trifluoride → 1-Bromo-4-(2-fluoropropan-2-yl)benzene

HRID 1691428Notes

Reaction equation

HRID 1691428 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](O)([CH3:10])[CH3:9])=[CH:4][CH:3]=1.CCN(S(F)(F)[F:18])CC>C(Cl)Cl>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([F:18])([CH3:10])[CH3:9])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 123472(Diethylamino)sulfur trifluorideHCID 126819202-(4-Bromophenyl)propan-2-ol

Product 1

HCID 469414101-Bromo-4-(2-fluoropropan-2-yl)benzene

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To 2-(4-bromophenyl)propan-2-ol (8.3 g, 38.59 mmol) in 100 mL of CH2Cl2 was added DAST (6.1 mL, 46.31 mmol) at −78° C. The reaction was stirred to rt overnight, and quenched with 100 mL of water at 0° C. The product was extracted with EtOAc, and the extracts were washed with water (50 mL) and brine (50 mL), dried over anhydrous MgSO4, and concentrated to give 1-bromo-4-(1-fluoro-1-methylethyl)benzene, which was used without further purification.

Workup

  1. customquenched with 100 mL of water at 0° C
  2. extractionThe product was extracted with EtOAc
  3. washthe extracts were washed with water (50 mL) and brine (50 mL)
  4. dry with materialdried over anhydrous MgSO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-261266de3be9400680005b3200da8304
Source dataset
uspto-grants-2012_04
Patent number
US08153626B2

Reaction notes

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