Boron tribromide → HCID 20531732, compound

HRID 1759314Notes

Reaction equation

HRID 1759314 reaction equation
[CH2:1]([N:4]1[CH2:13][CH:12]([C:14]2[CH:19]=[CH:18][C:17]([O:20]C)=[CH:16][CH:15]=2)[C:11]2[C:6](=[C:7]([Cl:26])[C:8]([O:24]C)=[C:9]([O:22]C)[CH:10]=2)[CH2:5]1)[CH:2]=[CH2:3].B(Br)(Br)[Br:28]>C(Cl)Cl.C(OCC)(=O)C.CO>[BrH:28].[CH2:1]([N:4]1[CH2:13][CH:12]([C:14]2[CH:19]=[CH:18][C:17]([OH:20])=[CH:16][CH:15]=2)[C:11]2[C:6](=[C:7]([Cl:26])[C:8]([OH:24])=[C:9]([OH:22])[CH:10]=2)[CH2:5]1)[CH:2]=[CH2:3]

Participants

5

Reactant 2

HCID 25134Boron tribromideHCID 13023210HCID 13023210, compound

Product 1

HCID 20531732HCID 20531732, compoundYield 52%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 21584119Ethylacetate methanolSolvent

Procedure

The N-allyl trimethoxy base (VII) (2.4 g, 0.0064 m) was dissolved in 50 ml of methylene chloride and mixed with a solution of 6.0 ml (0.64 m) of boron tribromide in 40 ml of methylene chloride at -15°. After stirring for 2 hours at room temperature, the mixture was cooled and quenched with methanol several times, the last time with 4 drops of 48% hydrogen bromide added. Final evaporation gave a foam which was dissolved in ethyl acetate-methanol. The mixture was heated at reflux briefly then cooled to give 1.5 g (52%) of 2-allyl-8-chloro-6,7-dihydroxy-4-(p-hydroxyphenyl)-1,2,3,4-tetrahydroisoquinoline hydrobromide, m.p. 252°-254° (d.).

Workup

  1. temperaturethe mixture was cooled
  2. customquenched with methanol several times
  3. additionthe last time with 4 drops of 48% hydrogen bromide added
  4. customFinal evaporation
  5. customgave a foam which
  6. temperatureThe mixture was heated
  7. temperatureat reflux briefly
  8. temperaturethen cooled

Sources & evidence

ORD record
ord-4f16e1e7ad2441c69e5f9c4a3cbf7991
Source dataset
uspto-grants-1982_07
Patent number
US04340601

Reaction notes

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