Triethylamine → HCID 178486027, compound

HRID 1743761Notes

Reaction equation

HRID 1743761 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Br:20][C:21]([Br:24])(Br)Br.C(N(CC)CC)C.[C:32]([O:36][C:37](=[O:48])[N:38]([C@H:40]1[CH2:45][CH2:44][C@H:43]([CH:46]=O)[CH2:42][CH2:41]1)[CH3:39])([CH3:35])([CH3:34])[CH3:33]>C(Cl)Cl>[C:32]([O:36][C:37](=[O:48])[N:38]([C@H:40]1[CH2:45][CH2:44][C@H:43]([CH:46]=[C:21]([Br:24])[Br:20])[CH2:42][CH2:41]1)[CH3:39])([CH3:35])([CH3:33])[CH3:34]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 178486044HCID 178486044, compound

Product 1

HCID 178486027HCID 178486027, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 52.45 g (200 mmol) triphenylphosphine in 200 ml CH2Cl2 was treated with 33.16 g (100 mmol) tetrabromomethane (the reaction heated up to reflux) and after 50 min with 32.06 ml (230 mmol) triethylamine (the reaction heated up to reflux and became dark violet). After cooling (0° C.), 12.83 g (50 mmol) of trans-(4-Formyl-cyclohexyl)-methyl-carbamic acid tert-butyl ester in 125 ml CH2Cl2 were added during 10 min. The solution was stirred for 16 h at RT, evaporated and filtered through silica gel (deactivated with hexane/0.5% Et3N) with hexane and then hexane/Et2O 4:1 to 1:1 as eluent to yield 13.28 g (67%) of trans-[4-(2,2-Dibromo-vinyl)-cyclohexyl]-methyl-carbamic acid tert-butyl ester, mp: 93–99° C., dec.; MS: 396 (MH+, 2Br).

Workup

  1. temperatureheated up
  2. temperatureheated up
  3. temperatureto reflux
  4. additionwere added during 10 min
  5. customevaporated
  6. filtrationfiltered through silica gel (deactivated with hexane/0.5% Et3N) with hexane

Sources & evidence

ORD record
ord-3ce25dd1e53f452fbccb72f9476f1e92
Source dataset
uspto-grants-2006_03
Patent number
US07012077B2

Reaction notes

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