Water → HCID 20446240, compound

HRID 2418401Notes

Reaction equation

HRID 2418401 reaction equation
P(Br)(Br)[Br:2].[N+:5]([C:8]1[C:15]([O:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[Cl:23])=[CH:14][CH:13]=[CH:12][C:9]=1[CH2:10]O)([O-:7])=[O:6].O>C(Cl)Cl>[N+:5]([C:8]1[C:15]([O:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[Cl:23])=[CH:14][CH:13]=[CH:12][C:9]=1[CH2:10][Br:2])([O-:7])=[O:6]

Participants

5

Reactant 3

HCID 962WaterHCID 24614Phosphorus tribromideHCID 53679561HCID 53679561, compound

Product 1

HCID 20446240HCID 20446240, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

A solution of Phosphorus tribromide (1.72 ml) in methylene chloride (15 ml) was added dropwise to a solution of 2-nitro-3-(2-chlorophenoxy)benzyl alcohol (9.6 g) in methylene chloride (80 ml) at -10° C., and the mixture was stirred at 0° C. for an hour. To the reaction mixture was added water (50 ml), and the methylene chloride layer was separated, washed with aqueous sodium bicarbonate and saline, dried and then evaporated in vacuo. The oily residue was subjected to column chromatography on silica gel (110 g) and eluted with a mixture of n-hexane and benzene (2:1). The eluate was evaporated in vacuo, and the residue was recrystallized from a mixture of benzene and n-hexane to give 2-nitro-3-(2-chlorophenoxy)benzyl bromide (2.7 g). mp 68°-70° C.

Workup

  1. customthe methylene chloride layer was separated
  2. washwashed with aqueous sodium bicarbonate and saline
  3. customdried
  4. customevaporated in vacuo
  5. washeluted with a mixture of n-hexane and benzene (2:1)
  6. customThe eluate was evaporated in vacuo
  7. customthe residue was recrystallized from a mixture of benzene and n-hexane

Sources & evidence

ORD record
ord-6761f8744e0845d4b6194e49af512ba4
Source dataset
uspto-grants-1984_09
Patent number
US04472433

Reaction notes

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