Boron tribromide → HCID 66642855, compound

HRID 2108652Notes

Reaction equation

HRID 2108652 reaction equation
C[O:2][C:3]1[CH:18]=[CH:17][C:6]([CH2:7][C:8]2[CH:13]=[CH:12][C:11]([O:14]C)=[CH:10][C:9]=2[CH3:16])=[C:5]([CH3:19])[C:4]=1[CH:20]([CH3:22])[CH3:21].B(Br)(Br)Br>C(Cl)Cl>[OH:2][C:3]1[CH:18]=[CH:17][C:6]([CH2:7][C:8]2[CH:13]=[CH:12][C:11]([OH:14])=[CH:10][C:9]=2[CH3:16])=[C:5]([CH3:19])[C:4]=1[CH:20]([CH3:22])[CH3:21]

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 66642960HCID 66642960, compound

Product 1

HCID 66642855HCID 66642855, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a stirring solution of 4-(4′-methoxy-2′-methyl-3′-iso-propylbenzyl)-3-methyl-anisole (0.8 g, 2.68 mmol) in CH2Cl2 (10 mL) at −20° C. was added BBr3 (10.7 mL, 1M in CH2Cl2). The reaction mixture was stirred at room temperature for 16 hrs. Ice was add and the mixture was diluted with CH2Cl2. The organic layer was dried over Na2SO4, filtered and concentrated under reduced pressure. The crude product was purified by column chromatography on silica gel, eluting with ethyl acetate/hexanes (1:1) to afford 4-(4′-hydroxy-2′-methyl-3′-iso-propylbenzyl)-3-methylphenol as a yellow solid (0.54 g, 75%): 1H NMR (200 MHz, DMSO-d6): δ 9.03 (s, 1 H), 8.84 (s, 1 H), 6.41-6.60 (m, 5 H), 3.65 (s, 2 H), 3.33 (m, 1 H), 2.12 (s, 3 H), 2.08 (s, 3 H), 1.27 (d, J=6.9 Hz, 6 H); TLC conditions: Uniplate silica gel, 250 microns; Mobile phase=20% ethyl acetate in hexanes; Rf=0.31.

Workup

  1. additionIce was add
  2. dry with materialThe organic layer was dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe crude product was purified by column chromatography on silica gel
  6. washeluting with ethyl acetate/hexanes (1:1)

Sources & evidence

ORD record
ord-bd7f315ea46d4ef3a2a12e5fe96d218f
Source dataset
uspto-grants-2009_04
Patent number
US07514419B2

Reaction notes

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