Dimethylformamide → 4-Bromo-1,1-dimethoxybutane

HRID 1576170Notes

Reaction equation

HRID 1576170 reaction equation
[CH3:1][O:2][CH:3]([O:8][CH3:9])[CH2:4][CH2:5][CH2:6]O.CN(C)C=O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(Br)(Br)(Br)[Br:35]>O>[CH3:1][O:2][CH:3]([O:8][CH3:9])[CH2:4][CH2:5][CH2:6][Br:35]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 899884,4-Dimethoxybutan-1-ol

Product 1

HCID 104202254-Bromo-1,1-dimethoxybutane

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 0.1 moles of 4,4-dimethoxybutanol in 50 ml. of dimethylformamide containing 0.1 moles of triphenylphosphine is allowed to react for 18 hours with 0.1 moles of carbon tetrabromide. The mixture is diluted with water and extracted with ether. The ether extracts are combined, washed with water, dried and evaporated to a crude product which is purified by distillation to yield 4,4-dimethoxybutylbromide. This bromide is then converted into the diethyl phosphonate using the procedure described in Example 2.

Workup

  1. extractionextracted with ether
  2. washwashed with water
  3. customdried
  4. customevaporated to a crude product which
  5. distillationis purified by distillation

Sources & evidence

ORD record
ord-2504079ee5c946529545f5211e70f594
Source dataset
uspto-grants-1976_09
Patent number
US03979458

Reaction notes

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