Carbon tetrabromide → HCID 20032357, compound

HRID 231433Notes

Reaction equation

HRID 231433 reaction equation
[Cl:1][C:2]1[C:7]([CH2:8]O)=[CH:6][C:5]([N:10]2[C:14](=[O:15])[C:13]3[CH2:16][CH2:17][CH2:18][CH2:19][C:12]=3[C:11]2=[O:20])=[C:4]([F:21])[CH:3]=1.C(Br)(Br)(Br)[Br:23].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C(OCC)C>[Cl:1][C:2]1[C:7]([CH2:8][Br:23])=[CH:6][C:5]([N:10]2[C:14](=[O:15])[C:13]3[CH2:16][CH2:17][CH2:18][CH2:19][C:12]=3[C:11]2=[O:20])=[C:4]([F:21])[CH:3]=1

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 136297542-[4-Chloro-2-fluoro-5-(hydroxymethyl)phenyl]-4,5,6,7-tetrahydro-1H-isoindole-1,3(2H)-dione

Product 1

HCID 20032357HCID 20032357, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a stirred solution of 3.0 g (0.0097 mole) of of N-(4-chloro-2-fluoro-5-hydroxymethylphenyl)-3,4,5,6-tetrahydrophthalimide, prepared by the method of Example 4, and 6.4 g (0.0194 mole) of carbon tetrabromide in 30 ml of diethyl ether was added portionwise 5.1 g (0.0194 mole) of triphenylphosphine. This mixture was stirred overnight and was then filtered to remove the solid which had formed, and the solvent was evaporated under reduced pressure. The residue was passed through a column of silica gel. Appropriate fractions were combined, and the solvent was evaporated yielding 1.1 g of N-(4-chloro-2-fluoro-5-bromomethylphenyl)-3,4,5,6tetrahydrophthalimide as a white solid, m .p. 126°-128° C. The nmr and ir spectra were consistent with the proposed structure.

Workup

  1. filtrationwas then filtered
  2. customto remove the solid which
  3. customhad formed
  4. customthe solvent was evaporated under reduced pressure
  5. customthe solvent was evaporated

Sources & evidence

ORD record
ord-aa65f84364d04a1e9bce2fd31f1bed1a
Source dataset
uspto-grants-1989_07
Patent number
US04846882

Reaction notes

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