Boron tribromide → HCID 17898073, compound

HRID 1418767Notes

Reaction equation

HRID 1418767 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([O:21]C)[CH:5]=[C:6]([CH3:20])[C:7]=1[CH2:8][C:9]1[CH:14]=[CH:13][C:12]([O:15]C)=[C:11]([CH:17]([CH3:19])[CH3:18])[CH:10]=1.B(Br)(Br)Br>C(Cl)Cl>[CH3:20][C:6]1[CH:5]=[C:4]([OH:21])[CH:3]=[C:2]([CH3:1])[C:7]=1[CH2:8][C:9]1[CH:14]=[CH:13][C:12]([OH:15])=[C:11]([CH:17]([CH3:18])[CH3:19])[CH:10]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 54526602HCID 54526602, compound

Product 1

HCID 17898073HCID 17898073, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
-78 °C

Procedure

To 3,5-dimethyl-4-(3'-isopropyl-4'-methoxybenzyl) anisole (8) (1.3 g, 4.35 mmol) in 75 mL of methylene chloride at -78° C. was added 44 mL of boron tribromide 1.0M in methylene chloride). The reaction mixture was stirred for 30 min at -78° C. and for 10 hours at room temperature. The reaction mixture was washed with water (2×100 mL), dried (MgSO4), and evaporated to give crude product (1.5 g). Purification using flash column chromatography (silica gel, 80:20 hexane/ethylacetate) gave 3,5-dimethyl-4-(4'-hydroxy-3'-isopropylbenzyl) phenol (9) (812 mg, 3.00 mmol, 69%); 1HNMR (CDCl3) δ 1.2 (d, 6H), 2.23 (s, 6H), 3.15 (heptet, 1H), 3.87 (s, 2H), 6.58 (m, 4H), 6.92 (s, 1H).

Workup

  1. washThe reaction mixture was washed with water (2×100 mL)
  2. dry with materialdried (MgSO4)
  3. customevaporated
  4. customto give crude product (1.5 g)
  5. customPurification

Sources & evidence

ORD record
ord-36d50d5df2704dd0a5e8717f8273b7d5
Source dataset
uspto-grants-1999_03
Patent number
US05883294

Reaction notes

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