Dichloromethane → HCID 86071219, compound

HRID 746367Notes

Reaction equation

HRID 746367 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 86071219HCID 86071219, compoundYield 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-7be346b8d40a48e3b16b2cdd7e8b52d1
Source dataset
uspto-grants-2008_07
Patent number
US07393828B2

Reaction notes

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