Methyl iodide → HCID 58197930, compound

HRID 1468082Notes

Reaction equation

HRID 1468082 reaction equation
[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][C:7]3([CH2:16][CH2:15][CH:14]([OH:17])[CH2:13][CH2:12]3)[C:8]2=[O:11])=[CH:4][C:3]=1[F:18].CI.[CH3:21]CC([O-])(C)C.[K+]>>[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][C:7]3([CH2:16][CH2:15][CH:14]([O:17][CH3:21])[CH2:13][CH2:12]3)[C:8]2=[O:11])=[CH:4][C:3]=1[F:18]

Participants

4

Reactant 3

HCID 6328Methyl iodideHCID 23683543Potassium t-amylateHCID 86706694HCID 86706694, compound2×

Product 1

HCID 58197930HCID 58197930, compoundYield 99%

Conditions

Temperature
35 °C

Procedure

A solution of 6′-bromo-5′-fluoro-4-hydroxyspiro[cyclohexane-1,2′-inden]-1′(3′H)-one (Intermediate 7, 1.94 g, 6.19 mmol) and methyl iodide (9.65 ml, 154 mmol) in 2-Me THF (80 mL) was heated to 35° C. Potassium tert-pentoxide (1.7 M in toluene) (5.01 g, 9.91 mmol) was slowly added dropwise over 10 min and the resulting mixture was stirred at 35° C. for 1 h. The reaction mixture was cooled to r.t., and partitioned between water and EtOAC. The organic phase was dried over magnesium sulfate and concentrated, to give the title compound (2.0 g, 99% yield). The product was used in the next step. MS (EI) m/z 326, 328 M+.

Workup

  1. temperatureThe reaction mixture was cooled to r.t.
  2. custompartitioned between water and EtOAC
  3. dry with materialThe organic phase was dried over magnesium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-82f03b55111249ceac0972f49fcbccae
Source dataset
uspto-grants-2015_04
Patent number
US09000183B2

Reaction notes

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