Carbon tetrabromide → HCID 10264950, compound

HRID 1369993Notes

Reaction equation

HRID 1369993 reaction equation
[C:1]([O:4][CH2:5][CH:6]([CH2:10][O:11][C:12](=[O:14])[CH3:13])[CH2:7][CH2:8]O)(=[O:3])[CH3:2].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(Br)(Br)(Br)[Br:35]>CN(C)C=O>[C:1]([O:4][CH2:5][CH:6]([CH2:10][O:11][C:12](=[O:14])[CH3:13])[CH2:7][CH2:8][Br:35])(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 101766101,4-Butanediol, 2-[(acetyloxy)methyl]-, 1-acetate

Product 1

HCID 10264950HCID 10264950, compoundYield 993.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 2-acetoxymethyl-4-hydroxy-but-1-yl acetate (10 g, 49 mmol), triphenyl phosphine (19.25 g, 73 mmol) and carbon tetrabromide (24.4 g, 73 mmol) was stirred for 18 hours at 4° C. in dimethylformamide (150 ml). The solvent was then evaporated, and the residue purified by column chromatography on silica gel, eluting with ether-light petroleum 2:3 to afford 2-acetoxymethyl-4-bromobut-1-yl acetate as a pale oil (130 g, 99%). δH (CDCl3) 1.73-2.56 (3H, m, CHCH2CH2), 2.04 (6H, s, 2×OCOCH3), 3.44 (2H, t, CH2Br), 4.04 (4H, d, 2×CH2OCOCH3).

Workup

  1. customThe solvent was then evaporated
  2. customthe residue purified by column chromatography on silica gel
  3. washeluting with ether-light petroleum 2:3

Sources & evidence

ORD record
ord-cddd35b5dc5e4fb79423bab54d0c6efd
Source dataset
uspto-grants-2003_06
Patent number
US06579981B1

Reaction notes

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