Water → HCID 68109854, compound

HRID 2171746Notes

Reaction equation

HRID 2171746 reaction equation
Br[C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][CH2:7][C:8]2([CH3:12])[CH3:11])=[CH:4][C:3]=1[O:13][CH3:14].C([Li])CCC.[Cl:20]N1C(=O)CCC1=O.O>C1COCC1>[Cl:20][C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][CH2:7][C:8]2([CH3:12])[CH3:11])=[CH:4][C:3]=1[O:13][CH3:14]

Participants

6

Reactant 4

HCID 962WaterHCID 31398ChlorosuccinimideHCID 67053816HCID 67053816, compoundHCID 178418339Butyllithium

Product 1

HCID 68109854HCID 68109854, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-78 °C

Procedure

To a solution of 6-bromo-5-methoxy-1,1-dimethyl-indan (2.00 g, 7.84 mmol) in THF (30 mL) at −78° C. was slowly added n-butyllithium (4.0 mL, 2.5 M in hexane). The resulting solution was stirred at −78° C. for 0.5 h and a solution of N-chlorosuccinimide (1.26 g, 9.40 mmol) in THF (30 mL) was added. After an additional 2 h at −78° C., the reaction was warmed to room temperature, poured into water (50 mL) and extracted with ethyl acetate (2×70 mL). The combined organic layers were washed with water, brine, dried over sodium sulfate, filtered, and concentrated. Purification by silica gel chromatography (2% ethyl acetate/heptane) afforded the title compound as a yellow oil.

Workup

  1. customat −78° C.
  2. waitAfter an additional 2 h at −78° C.
  3. temperaturethe reaction was warmed to room temperature
  4. extractionextracted with ethyl acetate (2×70 mL)
  5. washThe combined organic layers were washed with water, brine
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customPurification by silica gel chromatography (2% ethyl acetate/heptane)

Sources & evidence

ORD record
ord-0a310ee0813a40aaaf0452911c44e57a
Source dataset
uspto-grants-2015_06
Patent number
US09051331B2

Reaction notes

Loading…