Water → HCID 66875930, compound

HRID 1666458Notes

Reaction equation

HRID 1666458 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH2:19]O)[CH:5]=[C:6]([O:8][C:9]2[CH:14]=[CH:13][C:12]([C:15]([F:18])([F:17])[F:16])=[CH:11][N:10]=2)[CH:7]=1.S(Cl)([Cl:23])=O.O>C1COCC1>[Br:1][C:2]1[CH:7]=[C:6]([CH:5]=[C:4]([CH2:19][Cl:23])[CH:3]=1)[O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]([F:18])([F:17])[F:16])=[CH:11][N:10]=1

Participants

5

Reactant 3

HCID 962WaterHCID 24386Thionyl ChlorideHCID 66876264(3-Bromo-5-(5-(trifluoromethyl)pyridin-2-yloxy)phenyl)methanol

Product 1

HCID 66875930HCID 66875930, compoundYield 81.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (3-bromo-5-(5-(trifluoromethyl)pyridin-2-yloxy)phenyl)methanol (5.5 g, 15.8 mmol) in dry THF (30 mL) cooled to 0° C. was added thionyl chloride (3.22 mL, 44.3 mmol) dropwise. The reaction was warmed to RT and stirred for 2 h. The reaction mixture was then cooled and water was added. The mixture was extracted with ethyl acetate three times. The organic layer was washed with saturated NaHCO3 solution and brine, dried over Na2SO4, and evaporated to dryness to give the title compound (4.7 g). 1H NMR (500 MHz, CDCl3): δ 8.44 (s, 1H), 7.93 (d, J=8.5 Hz, 1H), 7.43 (s, 1H), 7.29 (s, 1H), 7.15 (s, 1H), 7.05 (d, J=8.5 Hz, 1H), 4.54 (s, 2H).

Workup

  1. temperatureThe reaction mixture was then cooled
  2. extractionThe mixture was extracted with ethyl acetate three times
  3. washThe organic layer was washed with saturated NaHCO3 solution and brine
  4. dry with materialdried over Na2SO4
  5. customevaporated to dryness

Sources & evidence

ORD record
ord-04fa4daea688404790a65bf5adc5c82b
Source dataset
uspto-grants-2011_10
Patent number
US08044052B2

Reaction notes

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