Thionyl bromide → 2-Bromomethyl-5-(3-trifluoromethylphenyl)-furan

HRID 1112741Notes

Reaction equation

HRID 1112741 reaction equation
O[CH2:2][C:3]1[O:4][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([C:14]([F:17])([F:16])[F:15])[CH:9]=2)=[CH:6][CH:7]=1.S(Br)([Br:20])=O>CN(C)C=O>[Br:20][CH2:2][C:3]1[O:4][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([C:14]([F:17])([F:16])[F:15])[CH:9]=2)=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 68176Thionyl bromideHCID 7782745{5-[3-(Trifluoromethyl)phenyl]furan-2-yl}methanol

Product 1

HCID 227625712-Bromomethyl-5-(3-trifluoromethylphenyl)-furan

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The hydroxymethyl compound (4.84 g; 0.02 mole) prepared in (a) above, was dissolved in dimethylformamide (30 ml) cooled to 0°-5° C. and thionyl bromide (1.7 ml; 0.02 mole) was added dropwise with stirring. After 2 hours the greenish-yellow solution was poured onto ice/water and extracted via diethyl ether. The ether extract was washed with NaCl (saturated solution) dried over molecular sieve 3A and evaporated to give a light brown oil which slowly crystallised (4.6 g).

Workup

  1. temperaturecooled to 0°-5° C.
  2. additionAfter 2 hours the greenish-yellow solution was poured onto ice/water
  3. extractionextracted via diethyl ether
  4. extractionThe ether extract
  5. washwas washed with NaCl (saturated solution)
  6. dry with materialdried over molecular sieve 3A
  7. customevaporated
  8. customto give a light brown oil which
  9. customslowly crystallised (4.6 g)

Sources & evidence

ORD record
ord-33ac89cf71744453914d7bc31feff290
Source dataset
uspto-grants-1978_10
Patent number
US04123529

Reaction notes

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