Carbon tetrabromide → HCID 22645499, compound

HRID 2414396Notes

Reaction equation

HRID 2414396 reaction equation
[C:1]([O:5][C:6](=[O:17])[CH2:7][O:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([CH2:15]O)[CH:10]=1)([CH3:4])([CH3:3])[CH3:2].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(Br)(Br)(Br)[Br:38]>ClCCl>[Br:38][CH2:15][C:11]1[CH:10]=[C:9]([CH:14]=[CH:13][CH:12]=1)[O:8][CH2:7][C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:17]

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 22645476HCID 22645476, compound

Product 1

HCID 22645499HCID 22645499, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

t-Butyl-3-(hydroxymethyl)-phenoxyacetate is dissolved in dichloromethane (1.3 L) at room temperature. Triphenylphosphine (127 g, 0.48 mol) is added with stirring, followed by dropwise addition of CBr4 (146 g, 0.44 mol). The resultant mixture is stirred for 1 hour at room temperature and then evaporated in vacuo. The residue (553 g) is adsorbed onto silica-gel (100 g) and then placed on a sintered glass funnel containing 700 g of silica gel. The column is eluted with hexane (2×4000 L) followed by 4:1 hexane/EtOAc (2×4000L). The hexane/EtOAc solutions are combined and evaporated in vacuo to provide t-butyl 3-(bromomethyl)-phenoxyacetate as a colorless oil. MS Found: M+18+:318, 320.

Workup

  1. customevaporated in vacuo
  2. customplaced on a sintered glass funnel
  3. additioncontaining 700 g of silica gel
  4. washThe column is eluted with hexane (2×4000 L)
  5. customevaporated in vacuo

Sources & evidence

ORD record
ord-0be2e5a9b0a64edab0b15d90fa16564c
Source dataset
uspto-grants-2004_11
Patent number
US06812237B2

Reaction notes

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