Bromine → HCID 14579226, compound

HRID 231074Notes

Reaction equation

HRID 231074 reaction equation
[C:1]1([CH:7]2[CH2:13][CH2:12][C:11](=[O:14])[C:10]3[CH:15]=[CH:16][CH:17]=[CH:18][C:9]=3[O:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Br:19]Br>C(OCC)C>[Br:19][CH:12]1[C:11](=[O:14])[C:10]2[CH:15]=[CH:16][CH:17]=[CH:18][C:9]=2[O:8][CH:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[CH2:13]1

Participants

4

Reactant 2

HCID 24408BromineHCID 142084352-Phenyl-3,4-dihydro-1-benzoxepin-5(2H)-one

Product 1

HCID 14579226HCID 14579226, compoundYield 95.8%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

800 mg (3.36 m moles) of 2-phenyl-2,3,4,5-tetrahydro-1-benzoxepin-5-one (compound R1 of Reference Example 1) was dissolved in 80 ml of absolute ethyl ether, and 808 mg (1.5 equivalent amount) of bromine was added to the solution dropwise over 15 minutes under ice-cooling. The reaction mixture was washed with a sodium sulfate aqueous solution followed by water, and then dried with anhydrous magnesium sulfate. After filtrating off the magnesium sulfate, the filtrate was concentrated to obtain a residue, which was then applied to a silica gel column, and eluted with a mixture of hexane/ethyl acetate (98:2) to obtain 1.02 g (yield 95.7%) of the desired compound in a form of a diastereomer mixture (R14a and R14b, ratio 3:1).

Workup

  1. temperaturecooling
  2. washThe reaction mixture was washed with a sodium sulfate aqueous solution
  3. dry with materialdried with anhydrous magnesium sulfate
  4. filtrationAfter filtrating off the magnesium sulfate
  5. concentrationthe filtrate was concentrated
  6. customto obtain a residue, which
  7. washeluted with a mixture of hexane/ethyl acetate (98:2)

Sources & evidence

ORD record
ord-2d805286f19c4eb89dc583c5b065d46b
Source dataset
uspto-grants-1989_07
Patent number
US04845094

Reaction notes

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