Water → HCID 66890160, compound

HRID 253314Notes

Reaction equation

HRID 253314 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([O:15][CH2:16][CH2:17][O:18][CH3:19])[C:5]([O:10][CH2:11][CH2:12][O:13][CH3:14])=[C:6]([CH2:8]O)[CH:7]=1.N1C=CC=CC=1.S(Cl)([Cl:28])=O.O>O1CCCC1>[Cl:28][CH2:8][C:6]1[CH:7]=[C:2]([F:1])[CH:3]=[C:4]([O:15][CH2:16][CH2:17][O:18][CH3:19])[C:5]=1[O:10][CH2:11][CH2:12][O:13][CH3:14]

Participants

6

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 24386Thionyl ChlorideHCID 66891637HCID 66891637, compound

Product 1

HCID 66890160HCID 66890160, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (5-fluoro-2,3-bis{[2-(methyloxy)ethyl]oxy}phenyl)methanol (0.31 g, 1.1 mmol) and pyridine (0.15 mL 1.9 mmol) in tetrahydrofuran (10 mL) at 0° C. was added thionyl chloride (0.093 mL, 1.3 mmol) and the reaction mixture warmed to room temperature and stirred for one hour. Then it was poured into water (20 mL) and extracted with ethyl acetate (3×20 mL). The combined extract was washed with water and brine (20 mL each), dried over sodium sulfate, filtered and concentrated to give 1-(chloromethyl)-5-fluoro-2,3-bis{[2-(methyloxy)ethyl]oxy}benzene (0.33 g, 1.1 mmol, 100% yield), 1H NMR (400 MHz, CDCl3): 6.76-6.26 (m, 2H), 4.69 (s, 2H), 4.22-4.13 (m, 4H), 3.86-3.78 (m, 4H), 3.46 (s, 6H).

Workup

  1. extractionextracted with ethyl acetate (3×20 mL)
  2. extractionThe combined extract
  3. washwas washed with water and brine (20 mL each)
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-d8093cc938e8469bad72cabff3c76b8c
Source dataset
uspto-grants-2011_01
Patent number
US07872014B2

Reaction notes

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