Benzyl Bromide → 1-(Benzyloxy)-3-bromo-5-iodobenzene

HRID 1189980Notes

Reaction equation

HRID 1189980 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([OH:9])[CH:5]=[C:6]([I:8])[CH:7]=1.[CH2:10](Br)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.C([O-])([O-])=O.[K+].[K+]>CN1C(=O)CCC1>[CH2:10]([O:9][C:4]1[CH:5]=[C:6]([I:8])[CH:7]=[C:2]([Br:1])[CH:3]=1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 226301823-Bromo-5-iodophenol

Product 1

HCID 672965731-(Benzyloxy)-3-bromo-5-iodobenzene

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

A mixture of 3-bromo-5-iodophenol (1.40 g, 4.68 mmol), benzyl bromide (0.89 g, 5.20 mmol) and anhydrous K2CO3 (1.44 g, 10.4 mmol) in anhydrous NMP (8 mL) was stirred under argon at +70° C. for 1 hour. The reaction mixture was partitioned between aqueous NH4Cl and hexanes. Aqueous layer was additionally extracted with hexanes and combined organic layers were washed with 1N NaOH, brine, dried over anhydrous MgSO4 and concentrated under reduced pressure to give 1-(benzyloxy)-3-bromo-5-iodobenzene as a colorless oil. Yield (2.14 g, 99%); 1H NMR (400 MHz, CDCl3) δ 7.45 (t, J=1.4 Hz, 1H), 7.32-7.40 (m, 5H), 7.26 (dd, J=1.4, 2.2 Hz, 1H), 7.09 (t, J=2.0 Hz, 1H), 5.00 (s, 2H).

Workup

  1. customThe reaction mixture was partitioned between aqueous NH4Cl and hexanes
  2. extractionAqueous layer was additionally extracted with hexanes
  3. washwere washed with 1N NaOH, brine
  4. dry with materialdried over anhydrous MgSO4
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-e001cf20ac6e4a28aecdcb3844580aeb
Source dataset
uspto-grants-2014_03
Patent number
US08674137B2

Reaction notes

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