Methanol → HCID 67053925, compound

HRID 2171745Notes

Reaction equation

HRID 2171745 reaction equation
[F:1][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]C.B(Br)(Br)Br.CO.C([O-])(O)=O.[Na+]>C(Cl)Cl>[F:1][C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][CH2:7][C:8]2([CH3:11])[CH3:12])=[CH:4][C:3]=1[OH:13]

Participants

6

Reactant 4

HCID 887MethanolHCID 25134Boron tribromideHCID 516892Sodium BicarbonateHCID 67053845HCID 67053845, compound

Product 1

HCID 67053925HCID 67053925, compoundYield 75.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
-78 °C

Procedure

To a solution of 6-fluoro-5-methoxy-1,1-dimethyl-indan (1.40 g, 7.21 mmol) in 20.0 ml of DCM at −78° C. was added BBr3 (1.40 ml, 14.4 mmol) in DCM (10.0 ml). The reaction mixture was stirred at −78° C. for two hours before being treated with 2.0 ml of methanol. This mixture was stirred for few minutes after which a saturated solution of NaHCO3 was carefully added and the resulting mixture stirred for an additional 1 hour. The mixture was extracted with DCM (3×40 mL) and the combined organic extracts were washed with brine and dried over Na2SO4. Flash column chromatography on silica gel (2-10% ethyl acetate/heptanes) afforded 0.985 g of the title compound.

Workup

  1. additionwas carefully added
  2. stirringthe resulting mixture stirred for an additional 1 hour
  3. extractionThe mixture was extracted with DCM (3×40 mL)
  4. washthe combined organic extracts were washed with brine
  5. dry with materialdried over Na2SO4

Sources & evidence

ORD record
ord-d4c8b61f256b45b0a5750480f0aea142
Source dataset
uspto-grants-2015_06
Patent number
US09051331B2

Reaction notes

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