Benzyl Bromide → HCID 10637344, compound

HRID 2258555Notes

Reaction equation

HRID 2258555 reaction equation
[Cl:1][C:2]1[C:7]([CH3:8])=[C:6]([CH3:9])[CH:5]=[C:4]([N+:10]([O-:12])=[O:11])[C:3]=1[OH:13].[CH2:14](Br)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[CH2:14]([O:13][C:3]1[C:4]([N+:10]([O-:12])=[O:11])=[CH:5][C:6]([CH3:9])=[C:7]([CH3:8])[C:2]=1[Cl:1])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 10821959HCID 10821959, compound

Product 1

HCID 10637344HCID 10637344, compoundYield 90.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2-Chloro-3,4-dimethyl-6-nitrophenol (6.44 g, 31.9 mmol) was dissolved in dry DMF (105 mL) and flushed with argon. Benzyl bromide (4.17 mL,35.1 mmol) and K2CO3 (13.24 g, 95.7 mmol) were added. The reaction mixture was stirred at room temperature for 8 h (protected from light) and filtered. Water (5 mL) was added and the solvent was co-evaporated with xylene (2×150 mL) and CH2Cl2 (100 mL). The residue was mixed with CHCl3 (100 mL), filtered and after evaporation of the solvent 10.8 g of crude product remained. Purification by flash column chromatography (SiO2, CHCl3 -Hexane 1:1) gave the title compound (8.44 g). Mp: 74°-75° C.; 1H NMR (DMSO-d6): δ 7.80 (s, 1 H), 7.48-7.37 (m, 5 H), 5.06 (s, 2 H), 2.37 (s, 3 H), 2.34 (s, 3 H); 13C NMR (DMSO-d6): δ 145.24, 142.22, 142.08, 135.73, 134.73, 129.61, 128.39, 128.37, 128.35, 123.64, 75.74, 19.74, 17.13; MS (EI, 70 eV): m/z (rel.int.) 293/291 (M+, 0.08/0.37), 187/185 (8/24), 91 (100).

Workup

  1. customflushed with argon
  2. filtrationfiltered
  3. additionWater (5 mL) was added
  4. additionThe residue was mixed with CHCl3 (100 mL)
  5. filtrationfiltered
  6. customafter evaporation of the solvent 10.8 g of crude product
  7. customPurification by flash column chromatography (SiO2, CHCl3 -Hexane 1:1)

Sources & evidence

ORD record
ord-2af1205037d94a1f8df06517e3410e84
Source dataset
uspto-grants-1997_08
Patent number
US05661183

Reaction notes

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