Boron tribromide → HCID 44182098, compound

HRID 709846Notes

Reaction equation

HRID 709846 reaction equation
C[O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH2:9][CH:8]([C:13]1([CH3:19])[CH2:17][O:16][C:15](=[O:18])[NH:14]1)[CH2:7][CH2:6]2.B(Br)(Br)Br>ClCCl>[OH:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH2:9][CH:8]([C:13]1([CH3:19])[CH2:17][O:16][C:15](=[O:18])[NH:14]1)[CH2:7][CH2:6]2

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 461946751225228-92-1

Product 1

HCID 44182098HCID 44182098, compoundYield 84.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
20 °C

Procedure

A stirred solution of 100 grams of 4-(6-methoxy-1,2,3,4-tetrahydronaphthalen-2-yl)-4-methyloxazolidin-2-one in 6 L dichloromethane was cooled to −80° C. under nitrogen. A solution of 177 g BBr3 in dichloromethane was added dropwise; during addition the reaction temperature was kept below −75° C. The reaction was stirred at 20° C. until the starting material was less than 2% by HPLC. Ice water was added to crystallize the solid, which was filtered, washed with water, and the cake was slurried in methanol and dried to afford 80 g of 4-(6-hydroxy-1,2,3,4-tetrahydronaphthalen-2-yl)-4-methyloxazolidin-2-one, M=247.29, purity >98%.

Workup

  1. additionduring addition the reaction temperature
  2. customwas kept below −75° C
  3. customto crystallize the solid, which
  4. filtrationwas filtered
  5. washwashed with water
  6. customdried

Sources & evidence

ORD record
ord-35a605ce6c8048a092f2c2c9627187a8
Source dataset
uspto-grants-2015_11
Patent number
US09181191B2

Reaction notes

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