Hydrogen Bromide → HCID 14230261, compound

HRID 345525Notes

Reaction equation

HRID 345525 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([C:15]3[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=3)[CH2:13][CH2:12][CH2:11][O:10][C:9]2=[O:14])=[CH:4][CH:3]=1.[BrH:22]>C(O)(=O)C>[Br:22][CH2:11][CH2:12][CH2:13][C:8]([C:15]1[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=1)([C:5]1[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=1)[C:9]([OH:10])=[O:14]

Participants

4

Reactant 2

HCID 260Hydrogen BromideHCID 142302603,3-bis(4-fluorophenyl)tetrahydro-2H-pyran-2-one

Product 1

HCID 14230261HCID 14230261, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 5.8 parts of 3,3-bis(4-fluorophenyl)tetrahydro-2H-pyran-2-one and 30 parts of a solution of hydrobromic acid in glacial acetic acid was stirred over week-end at room temperature. The reaction mixture was poured onto water. The precipitated product was filtered off and dissolved in 2,2'-oxybispropane. The organic phase was added with water, dried, filtered and evaporated. The residue was boiled in a mixture of 42 parts of 2,2'-oxybispropane and 42 parts of petroleum-ether. The product was filtered off and crystallized from 2,2'-oxybispropane, yielding 1.27 parts of α-(3-bromopropyl)-4-fluoro-α-(4-fluorophenyl)benzeneacetic acid; mp. 161° C. (intermediate 22).

Workup

  1. additionThe reaction mixture was poured onto water
  2. filtrationThe precipitated product was filtered off
  3. dissolutiondissolved in 2,2'-oxybispropane
  4. additionThe organic phase was added with water
  5. customdried
  6. filtrationfiltered
  7. customevaporated
  8. additionThe residue was boiled in a mixture of 42 parts of 2,2'-oxybispropane and 42 parts of petroleum-ether
  9. filtrationThe product was filtered off
  10. customcrystallized from 2,2'-oxybispropane

Sources & evidence

ORD record
ord-fb194ed6309848ddb69f55c3c2890944
Source dataset
uspto-grants-1991_10
Patent number
US05057525

Reaction notes

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