Bis(2-bromoethyl) ether → HCID 86671737, compound

HRID 577269Notes

Reaction equation

HRID 577269 reaction equation
[NH2:1][C:2]1[C:3]([F:12])=[C:4]([CH2:10][OH:11])[C:5]([F:9])=[C:6]([F:8])[CH:7]=1.CCN(C(C)C)C(C)C.Br[CH2:23][CH2:24][O:25][CH2:26][CH2:27]Br>CN(C=O)C.CCOC(C)=O>[F:9][C:5]1[C:6]([F:8])=[CH:7][C:2]([N:1]2[CH2:27][CH2:26][O:25][CH2:24][CH2:23]2)=[C:3]([F:12])[C:4]=1[CH2:10][OH:11]

Participants

6

Reactant 3

HCID 21521Bis(2-bromoethyl) etherHCID 81531DiisopropylethylamineHCID 86671736HCID 86671736, compound

Product 1

HCID 86671737HCID 86671737, compoundYield 48%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of (3-amino-2,5,6-trifluorophenyl)methanol (200 mg, 1.1 mmol) in DMF (3 mL) was added DIEA (1.6 mL) and 2-bromoethylether (5 eq) and the reaction heated to 80° C. for 18 h. The reaction was allowed to cool to rt, diluted with EtOAc and washed with H2O then saturated NH4Cl (aq). The organic phase was dried (Na2SO4), filtered and concentrated in vacuo. The resultant residue was purified by column chromatography (petroleum ether: EtOAc) to give (2,3,6-trifluoro-5-morpholinophenyl)methanol (110 mg, 48%).

Workup

  1. temperatureto cool to rt
  2. washwashed with H2O
  3. dry with materialThe organic phase was dried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe resultant residue was purified by column chromatography (petroleum ether: EtOAc)

Sources & evidence

ORD record
ord-5c85c381d8054adba005075a3cc11bef
Source dataset
uspto-grants-2015_05
Patent number
US09040545B2

Reaction notes

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