Sodium Carbonate → 5Bromo-4-chloro-4-fluoro-3,4,5,6-tetrahydrophthalic anhydride

HRID 1109826

Reaction equation

HRID 1109826 reaction equation
C1C=CN=CC=1.[FH:7].[Cl:8][C:9]1[CH2:10][C:11]2[C:16](=[O:17])[O:15][C:13](=[O:14])[C:12]=2[CH2:18][CH:19]=1.[Br:20]N1C(=O)CCC1=O.C(=O)([O-])[O-].[Na+].[Na+]>C(Cl)Cl>[Br:20][CH:19]1[CH2:18][C:12]2[C:13]([O:15][C:16](=[O:17])[C:11]=2[CH2:10][C:9]1([Cl:8])[F:7])=[O:14]

Participants

6

Reactant 4

HCID 10340Sodium CarbonateHCID 64774Pyridine, hydrofluoride (1:1)HCID 67184N-bromobutanimideHCID 109869774-Chloro-3,6-dihydrophthalic anhydride

Product 1

HCID 110980575Bromo-4-chloro-4-fluoro-3,4,5,6-tetrahydrophthalic anhydride

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Pyridinium poly(hydrogen fluoride) was added to a solid mixture of 4-chloro-3,6-dihydrophthalic anhydride (0.22 g) and N-bromosuccinimide (0.21 g) at room temperature. The reaction mixture was stirred for 3.25 hours and then carefully poured into a two phase system containing saturated sodium carbonate and methylene chloride. The methylene chloride layer was dried over magnesium sulfate and the solvent removed under reduced pressure. The residue was analyzed by NMR and GC-MS and contained 5-bromo -4-fluoro-3,4,5,6-tetrahydrophthalic anhydride as the major product along with some 4-fluorophthalic anhydride.

Workup

  1. additioncarefully poured into a two phase system
  2. dry with materialThe methylene chloride layer was dried over magnesium sulfate
  3. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-500ce20f28264da08f0ddc01cbb64ed7
Source dataset
uspto-grants-1994_06
Patent number
US05322954

Linked notes

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