Allyl Alcohol → HCID 58562927, compound

HRID 1186161Notes

Reaction equation

HRID 1186161 reaction equation
[CH2:1]([OH:4])[CH:2]=[CH2:3].C(N(CC)CC)C.[Br:12][C:13]1[CH:14]=[CH:15][C:16]([F:23])=[C:17]([CH2:19][C:20](Cl)=[O:21])[CH:18]=1>C(OCC)(=O)C>[CH2:1]([O:4][C:20](=[O:21])[CH2:19][C:17]1[CH:18]=[C:13]([Br:12])[CH:14]=[CH:15][C:16]=1[F:23])[CH:2]=[CH2:3]

Participants

5

Reactant 3

HCID 7858Allyl AlcoholHCID 8471TriethylamineHCID 585630975-Bromo-2-fluorophenylacetyl chloride

Product 1

HCID 58562927HCID 58562927, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of allyl alcohol (22.1 g, 380.5 mmol) and triethylamine (Et3N) (5.4 ml, 39 mmol) at 0° C. was added over 1 h crude (5-bromo-2-fluoro-phenyl) -acetyl chloride (intermediate B2A) (7.01 g, ca. 26 mmol). Then the reaction was stirred over 1 h from 0° C. to 23° C. The reaction mixture was diluted with ethyl acetate, washed with water, and the organic layer was dried over sodium sulfate. Removal of the solvent in vacuum left the title compound as a yellow oil (7.290 g, 103%), which was used without further purification. MS (ISP): m/z=280.1 [(M+NH4)+] and 282.1 [(M+2+NH4)+]

Workup

  1. washwashed with water
  2. dry with materialthe organic layer was dried over sodium sulfate
  3. customRemoval of the solvent in vacuum
  4. waitleft the title compound as a yellow oil (7.290 g, 103%), which
  5. customwas used without further purification

Sources & evidence

ORD record
ord-af763276818c432a9efd21062027d704
Source dataset
uspto-grants-2014_03
Patent number
US08673894B2

Reaction notes

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