Boron tribromide → HCID 17898073, compound

HRID 1418771Notes

Reaction equation

HRID 1418771 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([O:8]C)[CH:5]=[C:4]([CH3:10])[C:3]=1[C:11]([C:13]1[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[C:15]([CH:21]([CH3:23])[CH3:22])[CH:14]=1)=[O:12].B(Br)(Br)Br>C(Cl)Cl>[CH3:1][C:2]1[CH:7]=[C:6]([OH:8])[CH:5]=[C:4]([CH3:10])[C:3]=1[C:11](=[O:12])[C:13]1[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[C:15]([CH:21]([CH3:23])[CH3:22])[CH:14]=1.[CH3:1][C:2]1[CH:7]=[C:6]([OH:8])[CH:5]=[C:4]([CH3:10])[C:3]=1[CH2:11][C:13]1[CH:18]=[CH:17][C:16]([OH:19])=[C:15]([CH:21]([CH3:22])[CH3:23])[CH:14]=1

Participants

5

Reactant 2

HCID 25134Boron tribromideHCID 57170851HCID 57170851, compound

Product 2

HCID 17898073HCID 17898073, compoundYield 49%HCID 53852261HCID 53852261, compoundYield 31%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-78 °C

Procedure

To (2,6-dimethyl-4-methoxyphenyl)-(3-isopropyl-4-methoxyphenyl) methanone (10) (1 g, 3.20 mmol) in 60 ml of methylene chloride at -78° C. was added 32 mL of boron tribromide (1.0M in methylene chloride). The reaction mixture was stirred at -78° C. for 30 minutes, and then for 12 hours at room temperature. The reaction mixture was washed with water (2×125 mL), dried (MgSO4), and evaporated to give crude product (900 mg). Purification using flash column chromatography (silica gel, 90:10 hexane/ethylacetate) gave 3,5-dimethyl-4-(4'-methoxy-3'-isopropylbenzoyl) phenol (13) (300 mg, 31%) and 3,5-dimethyl-4-(4'-hydroxy-3'-isopropylbenzyl) phenol (14) (450 mg, 49%).

Workup

  1. waitfor 12 hours at room temperature
  2. washThe reaction mixture was washed with water (2×125 mL)
  3. dry with materialdried (MgSO4)
  4. customevaporated
  5. customto give crude product (900 mg)
  6. customPurification

Sources & evidence

ORD record
ord-67d485161a9d4e4bb4766ce56cfbfee4
Source dataset
uspto-grants-1999_03
Patent number
US05883294

Reaction notes

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