Cyclohexene → HCID 19838154, compound

HRID 476686Notes

Reaction equation

HRID 476686 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 1M 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-8225466c28e04f4386b7849dc204b525
Source dataset
uspto-grants-1989_12
Patent number
US04885313

Reaction notes

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