Carbon tetrabromide → Ethyl 7-(3-bromopropoxy)-2-ethylchromane-2-carboxylate

HRID 479637Notes

Reaction equation

HRID 479637 reaction equation
O[CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:15]=[C:14]2[C:9]([CH2:10][CH2:11][C:12]([CH2:21][CH3:22])([C:16]([O:18][CH2:19][CH3:20])=[O:17])[O:13]2)=[CH:8][CH:7]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(Br)(Br)(Br)[Br:43]>CC#N>[Br:43][CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:15]=[C:14]2[C:9]([CH2:10][CH2:11][C:12]([CH2:21][CH3:22])([C:16]([O:18][CH2:19][CH3:20])=[O:17])[O:13]2)=[CH:8][CH:7]=1

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 22737369HCID 22737369, compound

Product 1

HCID 22737362Ethyl 7-(3-bromopropoxy)-2-ethylchromane-2-carboxylateYield 96.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a 100 ml CH3CN solution of ethyl 7-(3-hydroxypropoxy)-2-ethylchromane-2-carboxylate (2.88 g, 9.4 mmol) was added triphenylphosphine (3.21 g, 12.2 mmol) and carbon tetrabromide (4.05 g, 12.2 mmol) upon cooling in an ice-water bath. After stirring at rt for 1 hr, the solvent was removed under reduced pressure. The residue was suspended in dichloromethane and was charged onto a silica gel column. Elution with 10% AcOEt/hexanes gave the title compound 3.36 g (96%).

Workup

  1. temperatureupon cooling in an ice-water bath
  2. customthe solvent was removed under reduced pressure
  3. additionwas charged onto a silica gel column
  4. washElution with 10% AcOEt/hexanes

Sources & evidence

ORD record
ord-34cc5eaec0ca470fa5cd3dfa6e1cf10a
Source dataset
uspto-grants-2003_11
Patent number
US06645997B2

Reaction notes

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