Water → HCID 68295707, compound

HRID 572496Notes

Reaction equation

HRID 572496 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:12])=[C:6]2[C:11]=1[O:10][CH2:9][CH2:8][CH2:7]2.[Cl-].[Al+3].[Cl-].[Cl-].[C:17]1(=[O:27])[C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[C:19](=[O:26])[O:18]1.O>ClCCCl>[F:1][C:2]1[CH:3]=[C:4]([C:19]([C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][C:25]=2[C:17]([OH:27])=[O:18])=[O:26])[C:5]([CH3:12])=[C:6]2[C:11]=1[O:10][CH2:9][CH2:8][CH2:7]2

Participants

6

Reactant 4

HCID 962WaterHCID 6811Phthalic AnhydrideHCID 6451240Aluminum(III) ChlorideHCID 66604057HCID 66604057, compound

Product 1

HCID 68295707HCID 68295707, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

An ice cold mixture of 8-fluoro-5-methylchroman (0.955 g, 5.75 mmol) in 1,2-Dichloroethane (DCE) (10 mL) was treated with aluminum chloride (1.532 g, 11.49 mmol) followed by isobenzofuran-1,3-dione (0.809 g, 5.46 mmol). The mixture was allowed to warm to ambient temperature and stirred for 90 minutes. Water was then added and the mixture was extracted with ethyl acetate. The extracts were washed with brine, dried over sodium sulfate, filtered and concentrated to give the title compound as an off-white solid: 1H NMR (400 MHz, DMSO-d6) δ ppm 1.92-2.05 (m, 2 H), 2.34 (s, 3 H), 2.62-2.79 (m, 2 H), 4.15-4.30 (m, 2 H), 6.68 (d, J=11.73 Hz, 1 H), 7.40 (d, J=7.43 Hz, 1 H), 7.51-7.76 (m, 2 H), 7.88 (d, J=7.43 Hz, 1 H), 13.15 (br. s., 1 H); LC/MS (m/z) ES+=315 (M+1).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extracts were washed with brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-5b73e040f336458f838b2d0e6d4eed28
Source dataset
uspto-grants-2015_05
Patent number
US09029391B2

Reaction notes

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