Cyclohexene → HCID 19838154, compound

HRID 2414023Notes

Reaction equation

HRID 2414023 reaction equation
C[O:2][C:3]1[CH:4]=[C:5]([CH2:11][CH2:12][NH:13][CH2:14][CH2:15]/[CH:16]=[CH:17]/[CH2:18][CH2:19][NH:20][CH2:21][CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH:6]=[CH:7][C:8]=1[O:9]C.C1CCCCC=1.B(Br)(Br)[Br:36]>ClCCl>[BrH:36].[BrH:36].[C:23]1([CH2:22][CH2:21][NH:20][CH2:19][CH2:18]/[CH:17]=[CH:16]/[CH2:15][CH2:14][NH:13][CH2:12][CH2:11][C:5]2[CH:4]=[C:3]([OH:2])[C:8]([OH:9])=[CH:7][CH:6]=2)[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1

Participants

5

Reactant 3

HCID 8079CyclohexeneHCID 25134Boron tribromideHCID 19838107HCID 19838107, compound

Product 1

HCID 19838154HCID 19838154, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

The product of step (d) (0.85 g) and cyclohexene (2.35 g) in dry dichloromethane (40 ml) were cooled to -80° and boron tribromide (9.3 ml., of a 1 solution in dichloromethane) was added under nitrogen. The mixture was allowed to warm to room temperature overnight then excess reagent was destroyed by the addition of methanol. The solution was evaporated to dryness and the residue triturated with ethyl acetate to give a grey solid. Recrystalisation from 2-propanol gave the title compound as the dihydrobromide salt (0.3 g) mp 208°-9°.

Workup

  1. customexcess reagent was destroyed by the addition of methanol
  2. customThe solution was evaporated to dryness
  3. customthe residue triturated with ethyl acetate
  4. customto give a grey solid
  5. customRecrystalisation from 2-propanol

Sources & evidence

ORD record
ord-87392c05a1c243189faa4f1b03823e81
Source dataset
uspto-grants-1988_01
Patent number
US04720586

Reaction notes

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