Sodium borohydride → HCID 68283441, compound

HRID 1855304Notes

Reaction equation

HRID 1855304 reaction equation
[Br:1][C:2]1[CH:15]=[C:14]2[C:5]([O:6][C:7]3[C:8]([F:19])=[CH:9][C:10]([O:17][CH3:18])=[CH:11][C:12]=3[C:13]2=[O:16])=[CH:4][CH:3]=1.[BH4-].[Na+]>C1COCC1.CO>[Br:1][C:2]1[CH:15]=[C:14]2[C:5]([O:6][C:7]3[C:8]([F:19])=[CH:9][C:10]([O:17][CH3:18])=[CH:11][C:12]=3[CH:13]2[OH:16])=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 574756397-bromo-4-fluoro-2-methoxy-9H-xanthen-9-one

Product 1

HCID 68283441HCID 68283441, compoundYield 88.5%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of 7-bromo-4-fluoro-2-methoxy-9H-xanthen-9-one (45 g, 139 mmol) in THF (400 ml) and MeOH (400 ml) at RT was added NaBH4 (10.54 g, 279 mmol) slowly over the course of one hour. The solution was stirred vigorously for 30 additional minutes, then quenched slowly with a saturated ammonium chloride solution (200 ml). Additional water was added and the mixture was filtered, then washed with water and dried under vacuum to afford 7-bromo-4-fluoro-2-methoxy-9H-xanthen-9-ol (40 g, 123 mmol) as a light yellow solid that was advanced without further purification.

Workup

  1. customquenched slowly with a saturated ammonium chloride solution (200 ml)
  2. additionAdditional water was added
  3. filtrationthe mixture was filtered
  4. washwashed with water
  5. customdried under vacuum

Sources & evidence

ORD record
ord-76fbd6b7f5384b3ba04acebc16e91017
Source dataset
uspto-grants-2015_02
Patent number
US08962859B2

Reaction notes

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