1,3-Dibromobenzene → 4-(3-Bromophenyl)-tetrahydro-2H-pyran-4-ol

HRID 2060761Notes

Reaction equation

HRID 2060761 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Br:8])[CH:3]=1.C([Li])CCC.CCCCCC.[O:20]1[CH:25]=[CH:24][C:23](=[O:26])[CH:22]=[CH:21]1>C1COCC1>[Br:8][C:4]1[CH:3]=[C:2]([C:23]2([OH:26])[CH2:24][CH2:25][O:20][CH2:21][CH2:22]2)[CH:7]=[CH:6][CH:5]=1

Participants

6

Reactant 4

HCID 79271,3-DibromobenzeneHCID 79684H-pyran-4-oneHCID 8058HexaneHCID 178418339Butyllithium

Product 1

HCID 189962824-(3-Bromophenyl)-tetrahydro-2H-pyran-4-olYield 76%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred −78° C. solution of 1,3-dibromobenzene (19.71 g, 81.05 mmol) in THF (150 mL) is added 1.6 M butyl lithium in hexane (50.66 mL, 81.05 mmol) and the reaction is stirred 10 minutes. 4H-Pyran-4-one, tetrahydro- (5.41 g, 54.04 mmol) is added dropwise and the reaction is stirred at −78° C. for 2 h. The reaction is quenched by addition of saturated aqueous ammonium chloride (25 mL) and is then diluted with minimal water and extracted with EtOAc. The organic layer is dried over Na2SO4 and the solvent is removed under reduced pressure to afford a residue that is purified by silica gel chromatography eluting with a linear gradient of 5% to 100% EtOAc in hexanes to give the title compound (11.18 g, 76%). GC-MS (m/e): (79Br/81Br) 256, 258 (M−1).

Workup

  1. stirringthe reaction is stirred at −78° C. for 2 h
  2. customThe reaction is quenched by addition of saturated aqueous ammonium chloride (25 mL)
  3. additionis then diluted with minimal water
  4. extractionextracted with EtOAc
  5. dry with materialThe organic layer is dried over Na2SO4
  6. customthe solvent is removed under reduced pressure
  7. customto afford a residue that
  8. customis purified by silica gel chromatography
  9. washeluting with a linear gradient of 5% to 100% EtOAc in hexanes

Sources & evidence

ORD record
ord-ccddfd7d55b64b2e9e7c17975147f7ed
Source dataset
uspto-grants-2012_10
Patent number
US08278441B2

Reaction notes

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