Dichloromethane → 4.5-Dimethoxy-2-nitrobenzyl 2-bromoacetate

HRID 1821557Notes

Reaction equation

HRID 1821557 reaction equation
[Br:1][CH2:2][C:3](Br)=[O:4].[N+:6]([C:9]1[C:14]([CH2:15][OH:16])=[CH:13][C:12]([O:17][CH3:18])=[C:11]([O:19][CH3:20])[CH:10]=1)([O-:8])=[O:7].CCN(CC)CC.C(Cl)Cl>CN(C1C=CN=CC=1)C.C(Cl)(Cl)Cl>[Br:1][CH2:2][C:3]([O:16][CH2:15][C:14]1[CH:13]=[C:12]([O:17][CH3:18])[C:11]([O:19][CH3:20])=[CH:10][C:9]=1[N+:6]([O-:8])=[O:7])=[O:4]

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 8471TriethylamineHCID 61147Bromoacetyl bromideHCID 660976-Nitroveratryl alcohol

Product 1

HCID 860712194.5-Dimethoxy-2-nitrobenzyl 2-bromoacetateYield 55.1%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6212ChloroformSolvent

Procedure

Bromoacetylbromide (0.19 ml, 2.2 mmol) was slowly added to the solution of 6-nitroveratrylalcohol (0.43 g, 2 mmol), Et3N (0.56 ml, 4 mmol) and DMAP (24 mg, 0.2 mmol) in CHCl3 (5 ml). After stirring at room temperature for five hours, CH2Cl2 (20 ml) was added and the mixture was washed with HCl (1 M, 2×10 ml), NaHCO3 (sat., 10 ml) and water (10 ml). Organic phase was dried over Na2SO4, evaporated and purified by chromatography (Si-gel, CH2Cl2) to yield 4.5-dimethoxy-2-nitrobenzyl 2-bromoacetate (368 mg, 55%).

Workup

  1. washthe mixture was washed with HCl (1 M, 2×10 ml), NaHCO3 (sat., 10 ml) and water (10 ml)
  2. dry with materialOrganic phase was dried over Na2SO4
  3. customevaporated
  4. custompurified by chromatography (Si-gel, CH2Cl2)

Sources & evidence

ORD record
ord-33a2afce51674e87b3b73355ac518a23
Source dataset
uspto-grants-2009_10
Patent number
US07608582B2

Reaction notes

Loading…