Triethylamine → HCID 178484007, compound

HRID 1743796Notes

Reaction equation

HRID 1743796 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:49])[N:38]([CH2:40][C@H:41]1[CH2:46][CH2:45][C@H:44]([CH:47]=O)[CH2:43][CH2:42]1)[CH3:39])([CH3:35])([CH3:34])[CH3:33]>C(Cl)Cl>[C:32]([O:36][C:37](=[O:49])[N:38]([CH2:40][C@H:41]1[CH2:42][CH2:43][C@H:44]([CH:47]=[C:21]([Br:24])[Br:20])[CH2:45][CH2:46]1)[CH3:39])([CH3:35])([CH3:33])[CH3:34]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 178484048HCID 178484048, compound

Product 1

HCID 178484007HCID 178484007, compoundYield 61%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 257.6 g (982 mmol) triphenylphosphine in 1 l CH2Cl2 was treated with 162.8 g (491 mmol) tetrabromomethane (the reaction heated up to reflux and was then cooled with an ice bath) and after 40 min at RT with 157.4 ml (1129 mmol) triethylamine (the reaction heated up to reflux and became dark violet). After cooling (0° C.), 77.96 g (corresponds to 245.5 mmol) of crude trans-(4-Formyl-cyclohexylmethyl)-methyl-carbamic acid tert-butyl ester in 600 ml CH2Cl2 were added during 20 min. The solution was stirred for 20 h at RT, evaporated and filtered through silica gel (deactivated with hexane/0.5% Et3N) with hexane/Et2O 99:1 to 4:1 as eluent to yield 61.5 g (61%) of trans-[4-(2,2-Dibromo-vinyl)-cyclohexylmethyl]-methyl-carbamic acid tert-butyl ester, MS: 409 (M, 2Br).

Workup

  1. temperatureheated up
  2. temperatureto reflux
  3. temperatureheated up
  4. temperatureto reflux
  5. additionwere added during 20 min
  6. customevaporated
  7. filtrationfiltered through silica gel (deactivated with hexane/0.5% Et3N) with hexane/Et2O 99:1 to 4:1 as eluent

Sources & evidence

ORD record
ord-0ea65b4214064aff858208ebbd357e5e
Source dataset
uspto-grants-2006_03
Patent number
US07012077B2

Reaction notes

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