Bromine → 4-bromo-9a-butyl-8-chloro-7-methoxy-1,2,9,9a-tetrahydro-3H-fluoren-3-one

HRID 7880

Reaction equation

HRID 7880 reaction equation
[CH2:1]([C:5]12[CH2:17][CH2:16][C:15](=[O:18])[CH:14]=[C:13]1[C:12]1[C:7](=[C:8]([Cl:21])[C:9]([O:19][CH3:20])=[CH:10][CH:11]=1)[CH2:6]2)[CH2:2][CH2:3][CH3:4].C(=O)(O)[O-].[Na+].[Br:27]Br>ClCCl>[Br:27][C:14]1[C:15](=[O:18])[CH2:16][CH2:17][C:5]2([CH2:1][CH2:2][CH2:3][CH3:4])[C:13]=1[C:12]1[C:7](=[C:8]([Cl:21])[C:9]([O:19][CH3:20])=[CH:10][CH:11]=1)[CH2:6]2

Participants

5

Reactant 3

HCID 24408BromineHCID 516892Sodium BicarbonateHCID 219909239a-butyl-8-chloro-7-methoxy-1,2,9,9a-tetrahydro-3H-fluoren-3-one

Product 1

HCID 219908724-bromo-9a-butyl-8-chloro-7-methoxy-1,2,9,9a-tetrahydro-3H-fluoren-3-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 9a-butyl-8-chloro-7-methoxy-1,2,9,9a-tetrahydro-3H-fluoren-3-one (555 mg, 1.82 mmol) in anhydrous dichloromethane (18.2 mL) was treated with sodium bicarbonate (765 mg, 9.1 mmol) and bromine (0.093 mL, 1.82 mmol). The mixture was stirred at room temperature for 30 minutes and then diluted with CH2Cl2 (50 mL) and washed with water (50 mL). The organic phase was dried over MgSO4, filtered through a pad of silica gel (10 mL) with a 10 mL CH2Cl2 rinse, and the solvent evaporated under vacuum. The residue (0.55 g) was lyophilized from benzene to afford 4-bromo-9a-butyl-8-chloro-7-methoxy-1,2,9,9a-tetrahydro-3H-fluoren-3-one as an amorphous solid.

Workup

  1. washwashed with water (50 mL)
  2. dry with materialThe organic phase was dried over MgSO4
  3. filtrationfiltered through a pad of silica gel (10 mL) with a 10 mL CH2Cl2
  4. washrinse
  5. customthe solvent evaporated under vacuum

Sources & evidence

ORD record
ord-9cf6287b0a4c41f28bee99b9776571b1
Source dataset
uspto-grants-2006_08
Patent number
US07087599B2

Linked notes

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