Carbon tetrabromide → HCID 53737214, compound

HRID 1075423Notes

Reaction equation

HRID 1075423 reaction equation
[C:1]([O:5][C:6](=[O:27])[C:7]1[C:12]([CH2:13]O)=[CH:11][CH:10]=[C:9]([O:15][C:16](=[O:26])[CH2:17][NH:18][C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH:8]=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:48]>ClCCl>[C:1]([O:5][C:6](=[O:27])[C:7]1[C:12]([CH2:13][Br:48])=[CH:11][CH:10]=[C:9]([O:15][C:16](=[O:26])[CH2:17][NH:18][C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH:8]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 53716162HCID 53716162, compound

Product 1

HCID 53737214HCID 53737214, compoundYield 42.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 650 mg of 3-(tert-butoxycarbonylaminoacetoxy)-6-hydroxymethylbenzoic acid tert-butyl ester and 580 mg of triphenylphosphine was added 848 mg of carbon tetrabromide, and the mixture was stirred for 2 h at room temperature. The mixture was diluted with dichloromethane and washed with water. The organic layer was dried over anhydrous Na2SO4 and concentrated in vacuo. Column chromatography on silica gel gave 322 mg of 3-(tert-butoxycarbonylaminoacetoxy)-6-(bromomethyl)benzoic acid tert-butyl ester as a colourless oil; 1H-NMR(CDCl3) δ1.34(9H,s), 1.51 (9H,s), 4.08(2H,br.d,J=5.6 Hz), 4.80(2H,s), 4.95(1H,br.s), 7.12(1H,dd,J=8.6,2.6 Hz), 7.34(1H,d,J=8.6 Hz), 7.51(1H,d,J=2.6 Hz)

Workup

  1. washwashed with water
  2. dry with materialThe organic layer was dried over anhydrous Na2SO4
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-64eb7e1e279b41279db79fef0df98ab6
Source dataset
uspto-grants-1999_05
Patent number
US05900486

Reaction notes

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