Boron tribromide → HCID 15858477, compound

HRID 1418770Notes

Reaction equation

HRID 1418770 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([O:8]C)[CH:5]=[C:4]([CH3:10])[C:3]=1[CH:11]([C:13]1[CH:18]=[CH:17][C:16]([O:19]C)=[C:15]([CH:21]([CH3:23])[CH3:22])[CH:14]=1)[CH3:12].B(Br)(Br)Br>C(Cl)Cl>[OH:8][C:6]1[CH:7]=[C:2]([CH3:1])[C:3]([CH:11]([C:13]2[CH:18]=[CH:17][C:16]([OH:19])=[C:15]([CH:21]([CH3:23])[CH3:22])[CH:14]=2)[CH3:12])=[C:4]([CH3:10])[CH:5]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 15858476HCID 15858476, compound

Product 1

HCID 15858477HCID 15858477, compoundYield 70.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-78 °C

Procedure

To 1-(2,6-dimethyl-4-methoxyphenyl)-1-(3-isopropyl-4-methoxyphenyl) ethane (250 mg, 0.8 mmol) in 15 mL of methylene chloride at -78° C. was added 8 mL of boron tribromide (1.0M in methylene chloride). The reaction mixture was stirred for 30 minutes at -78° C. and for 20 hours at room temperature. The reaction mixture was washed with water (2×25 mL), dried (MgSO4), and evaporated to give crude product (300 mg). Purification using flash column chromatography (silica gel, 90:10 hexane/ethylacetate) gave 1-(4-hydroxy-2,6-dimethylphenyl)-1-(4-hydroxy-3-isopropylphenyl) ethane (160 mg, 0.562 mmol, 70%); 1HNMR (CDCl3) δ 1.20 (dd, 6H), 1.60 (d, 3H), 2.25 (s, 6H), 2.35 (s, 3H), 3.20 (heptet, 1H), 4.45 (q, 1H), 6.45 (s, 1H), 6.65 (m, 2H), 7.00 (d, 1H), 7.20 (d, 1H).

Workup

  1. washThe reaction mixture was washed with water (2×25 mL)
  2. dry with materialdried (MgSO4)
  3. customevaporated
  4. customto give crude product (300 mg)
  5. customPurification

Sources & evidence

ORD record
ord-e5f5218ed4b64a17aab39649c01aac3c
Source dataset
uspto-grants-1999_03
Patent number
US05883294

Reaction notes

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