Acetyl bromide → HCID 20531733, compound

HRID 1759315Notes

Reaction equation

HRID 1759315 reaction equation
Br.[CH2:2]([N:5]1[CH2:14][CH:13]([C:15]2[CH:20]=[CH:19][C:18]([OH:21])=[CH:17][CH:16]=2)[C:12]2[C:7](=[C:8]([Cl:24])[C:9]([OH:23])=[C:10]([OH:22])[CH:11]=2)[CH2:6]1)[CH:3]=[CH2:4].[C:25]([Br:28])(=[O:27])[CH3:26]>FC(F)(F)C(O)=O>[BrH:28].[CH2:2]([N:5]1[CH2:14][CH:13]([C:15]2[CH:20]=[CH:19][C:18]([O:21][C:25](=[O:27])[CH3:26])=[CH:17][CH:16]=2)[C:12]2[C:7](=[C:8]([Cl:24])[C:9]([O:23][C:10](=[O:22])[CH3:9])=[C:10]([O:22][C:18](=[O:21])[CH3:17])[CH:11]=2)[CH2:6]1)[CH:3]=[CH2:4]

Participants

4

Reactant 2

HCID 10482Acetyl bromideHCID 20531732HCID 20531732, compound

Product 1

HCID 20531733HCID 20531733, compound

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A mixture of 1 g of 2-allyl-8-chloro-6,7-dihydroxy-4-(p-hydroxyphenyl)-1,2,3,4-tetrahydroisoquinoline hydrobromide, 1.3 ml of acetyl bromide and 200 ml of trifluoroacetic acid is stirred at 10° for 2 hours. After evaporation to dryness, the residue is purified, if necessary, by recrystallization to give 2-allyl-8-chloro-6,7-diacetoxy-4-(p-acetoxyphenyl)-1,2,3,4-tetrahydroisoquinoline hydrobromide. Similarly tri-isobutyryloxy, -propionyloxy, -isovaleryloxy, -n-butyryloxy and -n-heptanoyloxy ester derivatives are prepared.

Workup

  1. customAfter evaporation to dryness
  2. customthe residue is purified
  3. customif necessary, by recrystallization

Sources & evidence

ORD record
ord-328e998392cb4e92809fa239a8d20fcc
Source dataset
uspto-grants-1982_07
Patent number
US04340601

Reaction notes

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