Ammonia → 2-Benzyl-4-bromo-1-methoxybenzene

HRID 25828Notes

Reaction equation

HRID 25828 reaction equation
IC.[CH2:3]([C:10]1[CH:15]=[C:14]([Br:16])[CH:13]=[CH:12][C:11]=1[OH:17])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[C:18]([O-])([O-])=O.[K+].[K+].N>CC(C)=O.C(Cl)Cl.O>[CH2:3]([C:10]1[CH:15]=[C:14]([Br:16])[CH:13]=[CH:12][C:11]=1[O:17][CH3:18])[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Participants

8

Reactant 4

HCID 222AmmoniaHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 134735702-Benzyl-4-bromophenol

Product 1

HCID 105166292-Benzyl-4-bromo-1-methoxybenzeneYield 98%

Reagents, catalysts & solvents 3

HCID 180AcetoneSolventHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

9.48 ml (152 mmol, 10 eqv) iodomethane was added to a suspension of 4.00 g (15.2 mmol) 2-Benzyl-4-bromo-phenol (20) and 10.50 g (76 mmol, 5 eqv) K2CO3 in 70 ml acetone and the resulting mixture was refluxed for 24 h. After adding water and aq. NH3-solution, the aq. layer was extracted with Et2O. The comb. org. fractions were washed with brine, dried over Na2SO4 and evaporated. Column chromatography (CH2Cl2) yielded 4.11 g (14.8 mmol, 98%) 21 as a colorless liquid: Rf (CH2Cl2) 0.77; 1H NMR (400 MHz, CDCl3) δ 3.79 (s, 3H), 3.92 (s, 2H), 6.72 (d, 1H, J=8.59 Hz), 7.18 (m, 4H), 7.27 (m, 3H); LRMS (EI) m/z 279 (17), 278 (95), 277 (18), 276 (96), 263 (14), 261 (17), 198 (18), 197 (65), 182 (34), 181 (31), 166 (20), 165 (56), 154 (19), 153 (24), 152 (29), 92 (11), 91 (100), 77 (13), 76 (16), 63 (13); HRMS (EI) Calcd. for C14H13BrO: 276.014976. Found: 276.014234.

Workup

  1. temperaturethe resulting mixture was refluxed for 24 h
  2. extractionthe aq. layer was extracted with Et2O
  3. washfractions were washed with brine
  4. dry with materialdried over Na2SO4
  5. customevaporated

Sources & evidence

ORD record
ord-52cb27289f25476f9ef5855aa498c47d
Source dataset
uspto-grants-2005_02
Patent number
US06858600B2

Reaction notes

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