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

HRID 1109830

Reaction equation

HRID 1109830 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]Br.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 24408BromineHCID 64774Pyridine, hydrofluoride (1:1)HCID 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 6344DichloromethaneSolvent2×

Procedure

Pyridinium poly(hydrogen fluoride) was added to a solution of 4-chloro-3,6-dihydrophthalic anhydride (6.5 g) in methylene chloride (10.1 g) at room temperature. Bromine (3.1 g) was added. A violent reaction occurs. The solution was allowed to stand for 6 hours and then was poured into a two phase mixture of methylene chloride (30 ml) and solid sodium carbonate. The suspension was stirred for 10 minutes until bubbling stopped. The mixture was filtered and the methylene chloride removed under reduced pressure. The material was purified by a bulb to bulb distillation (140° C. air temperature and 2.8 torr) to give a yellowish solid, (3.74 g).

Workup

  1. customA violent reaction
  2. customuntil bubbling
  3. filtrationThe mixture was filtered
  4. customthe methylene chloride removed under reduced pressure
  5. distillationThe material was purified by a bulb to bulb distillation (140° C. air temperature and 2.8 torr)
  6. customto give a yellowish solid, (3.74 g)

Sources & evidence

ORD record
ord-8d4d1e2b6eb74cb0a5fd90834ca6e944
Source dataset
uspto-grants-1994_06
Patent number
US05322954

Linked notes

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