Carbon tetrabromide → Ethyl 2-[4-(2-bromoethyl)phenoxy]-2-methylpropanoate

HRID 1006458Notes

Reaction equation

HRID 1006458 reaction equation
O[CH2:2][CH2:3][C:4]1[CH:18]=[CH:17][C:7]([O:8][C:9]([CH3:16])([CH3:15])[C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:6][CH:5]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(Br)(Br)(Br)[Br:39]>ClCCl>[Br:39][CH2:2][CH2:3][C:4]1[CH:18]=[CH:17][C:7]([O:8][C:9]([CH3:16])([CH3:15])[C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 15229879Ethyl 2-[4-(2-hydroxy-ethyl)-phenoxy]-2-methyl-propionate

Product 1

HCID 15229877Ethyl 2-[4-(2-bromoethyl)phenoxy]-2-methylpropanoateYield 84.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of ethyl 2-[4-(2-hydroxyethyl)-phenoxy]-2-methylpropionate (474 mg) and triphenylphosphine (591 mg) in dichloromethane (10 ml) was added carbon tetrabromide (748 mg) under ice-cooling, and the mixture was stirred for 40 minutes. Rough purification of the reaction mixture by flash column chromatography on silica gel (eluent: diethylether) and further purification of the fraction by medium pressure liquid column chromatography on silica gel (eluent: hexane/diethyl ether=10/1) gave ethyl 2-[4-(2-bromoethyl)phenoxy]-2-methylpropionate (500 mg). 1H-NMR (CDCl3) δ ppm: 1.25 (3H, t, J=7.1 Hz), 1.59 (6H, s), 3.09 (2H, t, J=7.8 Hz), 3.52 (2H, t, J=7.8 Hz), 4.23 (2H, q, J=7.1 Hz) 6.79 (2H, d, J=8.7 Hz), 7.07 (2H, d, J=8.7 Hz)

Workup

  1. temperaturecooling
  2. customRough purification of the reaction mixture by flash column chromatography
  3. customon silica gel (eluent: diethylether) and further purification of the fraction by medium pressure liquid column chromatography on silica gel (eluent: hexane/diethyl ether=10/1)

Sources & evidence

ORD record
ord-595aeb7acb6e49158aa418ab57ad2a99
Source dataset
uspto-grants-2004_09
Patent number
US06790865B2

Reaction notes

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