tert-Butyl methyl ether → HCID 23001232, compound

HRID 397816Notes

Reaction equation

HRID 397816 reaction equation
[Br:1]Br.C[O:4][C:5]1[CH2:10][CH2:9][CH:8]([O:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH2:7][CH:6]=1.COC(C)(C)C>C(Cl)Cl>[CH2:12]([O:11][CH:8]1[CH2:9][CH2:10][C:5](=[O:4])[CH:6]([Br:1])[CH2:7]1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

5

Reactant 3

HCID 15413tert-Butyl methyl etherHCID 24408BromineHCID 59086012HCID 59086012, compound

Product 1

HCID 23001232HCID 23001232, compoundYield 45.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of bromine (0.56 ml, 10.90 mmol) in DCM (30 ml) was added dropwise to a solution of ((4-(methoxy)cyclohex-3-enyloxy)methyl)benzene (3.4 g, 15.57 mmol), which was prepared as described in the last step, in DCM (100 ml). The reaction mixture was stirred for 1 hour at room temperature. Tert-butyl methyl ether (150 ml) was added. The solution was washed with ice cooled water (200 ml), a saturated aqueous solution of sodium thiosulphate (100 ml), and a saturated aqueous solution of sodium hydrogencarbonate. The organic layer was dried over magnesium sulphate. The solvent was removed in vacuo. The crude product was purified by flash chromatography on silica (90 g), using ethyl acetate/heptane (1:2) as eluent, to give 1.40 g of a mixture of diastereoisomeres of 4-benzyloxy-2-bromocyclohexanone.

Workup

  1. customwas prepared
  2. washThe solution was washed with ice
  3. temperaturecooled water (200 ml)
  4. dry with materialThe organic layer was dried over magnesium sulphate
  5. customThe solvent was removed in vacuo
  6. customThe crude product was purified by flash chromatography on silica (90 g)

Sources & evidence

ORD record
ord-818e4ca972534faa88fc5b434a88c67a
Source dataset
uspto-grants-2003_08
Patent number
US06610721B2

Reaction notes

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