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Carbon tetrabromide → Tert-butyl [2-(2-bromoethyl)-2,3-dihydro-2,4,6,7-tetramethylbenzofuran-5-yl]carbamate

HRID 565664
Notes
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Reaction equation

HRID 565664 reaction equation
O[CH2:2][CH2:3][C:4]1([CH3:24])[CH2:8][C:7]2[C:9]([CH3:23])=[C:10]([NH:15][C:16](=[O:22])[O:17][C:18]([CH3:21])([CH3:20])[CH3:19])[C:11]([CH3:14])=[C:12]([CH3:13])[C:6]=2[O:5]1.C(Br)(Br)(Br)[Br:26].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>O1CCCC1>[Br:26][CH2:2][CH2:3][C:4]1([CH3:24])[CH2:8][C:7]2[C:9]([CH3:23])=[C:10]([NH:15][C:16](=[O:22])[O:17][C:18]([CH3:21])([CH3:20])[CH3:19])[C:11]([CH3:14])=[C:12]([CH3:13])[C:6]=2[O:5]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 54463969Tert-butyl [2,3-dihydro-2-(2-hydroxyethyl)-2,4,6,7-tetramethylbenzofuran-5-yl]carbamate

Product 1

HCID 54438432Tert-butyl [2-(2-bromoethyl)-2,3-dihydro-2,4,6,7-tetramethylbenzofuran-5-yl]carbamateYield 82%

Reagents, catalysts & solvents 1

HCID 8028
Tetrahydrofuran
Solvent

Procedure

To a solution of tert-butyl [2,3-dihydro-2-(2-hydroxyethyl)-2,4,6,7-tetramethylbenzofuran-5-yl]carbamate (7.7 g) and carbon tetrabromide (8.0 g) in tetrahydrofuran (80 mL) was added 6.3 g of triphenylphosphine under ice-cooling and the mixture was stirred for 30 minutes. This reaction mixture was filtered and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=97:3 to 4:1) to provide 7.5 g of the title compound. Yield 82%.

Workup

  1. temperaturecooling
  2. filtrationThis reaction mixture was filtered
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=97:3 to 4:1)

Sources & evidence

ORD record
ord-7eda659980da4537aa82588395baa004
Source dataset
uspto-grants-2001_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06172085B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes