Water → HCID 68796301, compound

HRID 450900Notes

Reaction equation

HRID 450900 reaction equation
C[O:2][C:3]1[CH:4]=[C:5]([C:14](O)([CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH:6]=[C:7]([O:12]C)[C:8]=1[CH:9]([CH3:11])[CH3:10].B(Br)(Br)Br.O.[OH-].[Na+]>C(Cl)Cl>[CH2:22]([C:14]([C:5]1[CH:4]=[C:3]([OH:2])[C:8]([CH:9]([CH3:10])[CH3:11])=[C:7]([OH:12])[CH:6]=1)=[CH:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

6

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 25134Boron tribromideHCID 68796557HCID 68796557, compound

Product 1

HCID 68796301HCID 68796301, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-78 °C

Procedure

To 2-(3,5-dimethoxy-4-i-propylphenyl)-1,3-diphenylpropan-2-ol (0.63 g, 1.6 mmol) in CH2Cl2 (10 mL) at −78° C. under N2 was added BBr3 (1M in CH2Cl2, 5.0 mL, 5.0 mmol) dropwise. After the reaction was stirred at −78° C. for 1 h, the temperature was allowed to rise to room temperature and the reaction mixture was stirred at room temperature over night. Water (50 mL) was added followed by 20% NaOH to adjust pH>12. The organic layer was removed and the aqueous layer was washed with hexane (2×10 mL). The aqueous layer was acidified with 6N HCl to pH 1 and extracted with ether (3×50 mL). The extract was washed with water (10 mL) and brine (10 mL) and dried over anhydrous Na2SO4. Evaporation of ether followed by flash chromatography using ethyl acetate:hexane (1:9) gave 5-(1-benzyl-2-phenylethenyl)-2-i-propyl-1,3-benzenediol (1).(0.26 g, 47%) as a liquid, which solidified on standing at 0° C. 1HNMR (CDCl3, ppm): δ 1.38 (d, J=7.1 Hz, 6H), 3.52 (hept, J=7.1 Hz, 1H), 4.08 (s, 2H), 6.51 (s, 2H), 7.13 (s, 1H), 7.2-7.4 (m, 10H).

Workup

  1. customto rise to room temperature
  2. stirringthe reaction mixture was stirred at room temperature over night
  3. customThe organic layer was removed
  4. washthe aqueous layer was washed with hexane (2×10 mL)
  5. extractionextracted with ether (3×50 mL)
  6. washThe extract was washed with water (10 mL) and brine (10 mL)
  7. dry with materialdried over anhydrous Na2SO4
  8. customEvaporation of ether

Sources & evidence

ORD record
ord-8859fcfe24e44a109cdfd663dd046a62
Source dataset
uspto-grants-2013_07
Patent number
US08487009B2

Reaction notes

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