Chloroacetic Acid → HCID 12893255, compound

HRID 1112601Notes

Reaction equation

HRID 1112601 reaction equation
Cl[CH2:2][C:3]([OH:5])=[O:4].[Br-:6].[Na+].S(=O)(=O)(O)O.[N+:13]([CH:16]([CH:19]([Br:21])[CH3:20])[CH2:17]O)([O-:15])=[O:14]>C1(C)C=CC=CC=1.O>[Br:6][CH2:2][C:3]([O:5][CH2:17][CH:16]([N+:13]([O-:15])=[O:14])[CH:19]([Br:21])[CH3:20])=[O:4]

Participants

7

Reactant 4

HCID 300Chloroacetic AcidHCID 1118Sulfuric AcidHCID 253881Sodium BromideHCID 227624033-Bromo-2-nitrobutan-1-ol

Product 1

HCID 12893255HCID 12893255, compoundYield 91.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

94.5g (1 mol) of chloroacetic acid, 132.6g (1.3 mol) of sodium bromide, 127.4g (1.3 mol) of c.-sulfuric acid, 100 ml of water, 198g (1 mol) of 2-nitro-3-bromo-n-butanol and 200g of toluene were used and treated in a similar way as described in Example 10. 291.2g of 2-nitro-3-bromo-n-butyl bromoacetate were obtained (91.3% yield of theory). Bp 130° C/ 0.3 mmHg, nD20 = 1.5060, D420 = 1.7876. 175g (98.9%) of potassium hydrogen sulfate was isolated.

Workup

  1. additiontreated in a similar way

Sources & evidence

ORD record
ord-367ed966198d41c3a2537de6cc6e4484
Source dataset
uspto-grants-1978_10
Patent number
US04123443

Reaction notes

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