Benzyl Bromide → 1-(Benzyloxy)-2-fluoro-4-nitrobenzene

HRID 1924153Notes

Reaction equation

HRID 1924153 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[CH:4][C:3]=1[OH:11].[CH2:12](Br)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[CH2:12]([O:11][C:3]1[CH:4]=[CH:5][C:6]([N+:8]([O-:10])=[O:9])=[CH:7][C:2]=1[F:1])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 98252-Fluoro-4-nitrophenolHCID 11430Potassium Carbonate

Product 1

HCID 220309121-(Benzyloxy)-2-fluoro-4-nitrobenzeneYield 95.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 2-fluoro-4-nitrophenol (50.0 g, 318 mmol), benzyl bromide (42 mL, 350 mmol) and potassium carbonate (66.0 g, 478 mmol) in DMF (200 mL) was heated to 40° C. overnight. The solution was cooled to room temperature, poured over ice and the resultant solid was filtered. This material was washed with water and dried to give 1-benzyloxy-2-fluoro-4-nitrobenzene (75.0 g, 95%). 1H NMR (400 MHz, d6-DMSO): δ 8.19-8.11 (m, 2H), 7.53-7.37 (m, 6H), 5.36 (s, 2H); 13C NMR (100 MHz, d6-DMSO): δ 152.8, 152.4, 149.9, 140.9, 136.1, 129.3, 129.1, 128.7, 122.0, 115.2, 112.8, 112.6, 71.6; IR (cm−): 1499, 1346, 1279, 1211, 1142, 1072, 986, 885, 812, 789, 754, 742, 700, 648, 577.

Workup

  1. additionpoured over ice
  2. filtrationthe resultant solid was filtered
  3. washThis material was washed with water
  4. customdried

Sources & evidence

ORD record
ord-24a6314b365147a18ec4fb127cf09079
Source dataset
uspto-grants-2012_05
Patent number
US08178532B2

Reaction notes

Loading…