Hydrogen Bromide → HCID 21202093, compound

HRID 1978902Notes

Reaction equation

HRID 1978902 reaction equation
C[O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[C:9]([CH3:17])([C:13]([F:16])([F:15])[F:14])[O:8][CH2:7][CH2:6]2.Br>C(O)(=O)C>[OH:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[C:9]([CH3:17])([C:13]([F:16])([F:14])[F:15])[O:8][CH2:7][CH2:6]2

Participants

4

Reactant 2

HCID 260Hydrogen BromideHCID 102205196-Methoxy-1-methyl-1-trifluoromethylisochroman

Product 1

HCID 21202093HCID 21202093, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
130 °C

Procedure

To a stirred solution of 6-Methoxy-1-methyl-1-trifluoromethylisochroman (71 g, 0.29 mol) in acetic acid (600 mL) was added aqueous 48% HBr (300 mL) and the mixture was stirred at 130° C. for 13 hr. After removing acetic acid in vacuo, the reaction mixture was treated with aqueous NaOH (8 M) until the pH became 5-6. The resultant solution was extracted with ethyl acetate (400 mL×2) and the combined ethyl acetate extracts were washed with brine(100 mL), dried over MgSO4, and concentrated in vacuo. Flash chromatography (Silica-gel, 15×20 cm, 17% ethyl acetate/hexane) afforded 6-hydroxy-1-methyl-1-trifluoromethylisochroman (67 g, 100%) as a colorless oil. 1H-NMR(CDCl3): 7.22 (d, J=9.1 Hz, 1H), 6.73 (dd, J=9.1, 2.6 Hz, 1H), 6.63 (d, J=2.6 Hz, 1H), 5.00 (s, 1H, 4.17-4.07 (m, 1H), 3.90 (dt, J=11, 5.8 Hz, 1H), 2.84-2.78 (m, 2H), 1.64 (s, 3H).

Workup

  1. customAfter removing acetic acid in vacuo
  2. additionthe reaction mixture was treated with aqueous NaOH (8 M) until the pH
  3. extractionThe resultant solution was extracted with ethyl acetate (400 mL×2)
  4. washthe combined ethyl acetate extracts were washed with brine(100 mL)
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-58ce44ba31ae45edac583ade7e75d75e
Source dataset
uspto-grants-2001_05
Patent number
US06239147B1

Reaction notes

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