Cyclohexene → 1,3-Benzenediol, 4-[1-(2-propenyl)-7-(trifluoromethyl)-1H-indazol-3-yl]-

HRID 1819751Notes

Reaction equation

HRID 1819751 reaction equation
[CH2:1]([N:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][C:11]=2[C:13]([F:16])([F:15])[F:14])[C:6]([C:17]2[CH:22]=[CH:21][C:20]([O:23]C)=[CH:19][C:18]=2[O:25]C)=[N:5]1)[CH:2]=[CH2:3].B(Br)(Br)Br.C1CCCCC=1>>[CH2:1]([N:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][C:11]=2[C:13]([F:16])([F:15])[F:14])[C:6]([C:17]2[CH:22]=[CH:21][C:20]([OH:23])=[CH:19][C:18]=2[OH:25])=[N:5]1)[CH:2]=[CH2:3]

Participants

4

Reactant 3

HCID 8079CyclohexeneHCID 25134Boron tribromideHCID 116605203-(2,4-Dimethoxyphenyl)-1-(prop-2-en-1-yl)-7-(trifluoromethyl)-1H-indazole

Product 1

HCID 1354619821,3-Benzenediol, 4-[1-(2-propenyl)-7-(trifluoromethyl)-1H-indazol-3-yl]-Yield 109.7%

Procedure

1-Allyl-3-(2,4-dimethoxyphenyl)-7-(trifluoromethyl)-1H-indazole (0.065 g, 0.18 mmol) was treated with boron tribromide (0.136 mL, 1.4 mmol) and 1.0 mL of cyclohexene at −78° C. and then slowly allowed to warm to ambient temperature. The reaction was quenched by dropwise addition of methanol to the cooled reaction. The solvent was removed and the residue portioned with EtOAc and 1N HCl. The organic phase was washed with brine and dried with Na2SO4). Removal of the solvent in vacuo afforded the crude product. Pure product was obtained by crystallization to give the product (0.066 g) as a white solid, mp 114-115° C.;

Workup

  1. customThe reaction was quenched by dropwise addition of methanol to the cooled reaction
  2. customThe solvent was removed
  3. washThe organic phase was washed with brine
  4. dry with materialdried with Na2SO4)
  5. customRemoval of the solvent in vacuo
  6. customafforded the crude product
  7. customPure product was obtained by crystallization

Sources & evidence

ORD record
ord-9ce6bb18007140f8accf02a4cab29b04
Source dataset
uspto-grants-2009_10
Patent number
US07601847B2

Reaction notes

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