Benzyl Bromide → 4-(Benzyloxy)-1-bromo-2-chlorobenzene

HRID 1850718Notes

Reaction equation

HRID 1850718 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][C:3]=1[Cl:9].C([O-])([O-])=O.[K+].[K+].[CH2:16](Br)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>CN(C=O)C.O>[CH2:16]([O:8][C:5]1[CH:6]=[CH:7][C:2]([Br:1])=[C:3]([Cl:9])[CH:4]=1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

6

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 70181824-Bromo-3-chlorophenol

Product 1

HCID 223195014-(Benzyloxy)-1-bromo-2-chlorobenzene

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

4-bromo-3-chlorophenol (1 g, 4.82 mmol) was dissolved in DMF (10 ml) and K2CO3 (1.332 g, 9.64 mmol) and benzyl bromide (0.630 ml, 5.30 mmol) added. The mixture was stirred under N2 for 1 hr at RT. The mixture was diluted with water (15 mL) and extracted with EtOAc (2×10 mL). The organic fractions were combined, washed with brine (saturated, 1×8 mL), dried over MgSO4, filtered and the volatiles removed in vacuo. The residue was purified by chromatography on silica gel Biotage 25M, using a gradient eluant of EtOAc/Hexane (0-50%) to afford the title compound. LC/MS (m/z): 297 (M+H)+.

Workup

  1. extractionextracted with EtOAc (2×10 mL)
  2. washwashed with brine (saturated, 1×8 mL)
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. customthe volatiles removed in vacuo
  6. customThe residue was purified by chromatography on silica gel Biotage 25M

Sources & evidence

ORD record
ord-045cb08c5c874fb589dbe5ee1c14f47a
Source dataset
uspto-grants-2015_02
Patent number
US08957062B2

Reaction notes

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